MXPA06007033A - Herbicidal pyrimidines. - Google Patents

Herbicidal pyrimidines.

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Publication number
MXPA06007033A
MXPA06007033A MXPA06007033A MXPA06007033A MXPA06007033A MX PA06007033 A MXPA06007033 A MX PA06007033A MX PA06007033 A MXPA06007033 A MX PA06007033A MX PA06007033 A MXPA06007033 A MX PA06007033A MX PA06007033 A MXPA06007033 A MX PA06007033A
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Mexico
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carbon atoms
compound
methyl
amino
alkyl
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MXPA06007033A
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Spanish (es)
Inventor
David Alan Clark
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Du Pont
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Publication of MXPA06007033A publication Critical patent/MXPA06007033A/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation wherein R1 is cyclopropyl optionally substituted with 1-5 R5, isopropyl optionally substituted with 1-5 R6, or phenyl optionally substituted with 1-3 R7; R2 is ((O)jC(R15)(R16))kR; R is CO2H or a herbicidally effective derivative of CO2H; R3 is halogen, cyano, nitro, OR20, SR21 or N(R22)R23; R4 is -N(R24)R25 or -NO2; j is 0 or 1; and k is 0 or 1; provided that when k is 0, then j is 0; and R5, R6, R7, R15, R16, R20, R21, R22, R23, R24 and R25 are as defined in the disclosure. Also disclosed are compositions comprising the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I. Also disclosed are compositions comprising a compound of Formula I and at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

Description

PIRI IDINAS HERBICIDAS FIELD OF THE INVENTION This invention relates to certain pyrimidines, their N-oxides, agriculturally suitable salts and compositions, as well as methods for their use to eliminate unwanted vegetation.
BACKGROUND OF THE INVENTION The removal of unwanted vegetation is extremely important to obtain a high efficiency crop. Obtaining a selective elimination of weed growth especially in such useful crops as rice, soy, sugar beet, corn, potato, wheat, barley, tomato, and crop plantations, among others, is very desirable. Weed growth not verified in such crops can cause a significant reduction in productivity and therefore can result in increased costs to the consumer. Control of unwanted vegetation in non-harvest areas is also important.
Many products are commercially available for these purposes, but there is still a need for new compounds which are more effective, less expensive, less toxic, environmentally safer or have different modes of action. Ref .: 173222 World Patent Application Publication WO 92/05159-A describes pyrimidines useful as plant protectants, especially fungicides. European Patent Application Publication EP-136976-A2 describes pyrimidines as plant growth regulators. U.S. Patent 5,324,710 describes sulfonated heterocyclic carboxamide derivatives of pyrimidines as herbicides and growth regulators.
SUMMARY OF THE INVENTION this invention relates to a compound of formula I which includes all geometric isomers and stereoisomers, N-oxides or agriculturally suitable salts thereof, agricultural compositions containing them and their use as herbicides: wherein: R1 is cyclopropyl optionally substituted with 1-5 of R5, isopropyl optionally substituted with 1-5 of R6 or phenyl optionally substituted with 1-3 of R7; R2 is ((O) jC (R15) (R16)) kR; R is C02H or a herbicidally effective derivative of C02H; R3 is halogen, cyano, nitro, OR20, SR21 or N (R22) R23; R4 is -N (R2) R25 or -N02; each R5 and R6 is independently halogen, alkoyl of 1 to 6 carbon atoms, haloalguile of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalgenyl of 2 to 6 carbon atoms, alkoxy of 1 to 3 atoms carbon, haloalkoxy of 1 to 2 carbon atoms, alkylthio of 1 to 3 carbon atoms or haloalkylthio of 1 to 2 carbon atoms; each R7 is independently halogen, cyano, nitro, alkoyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halocycloalkyl of 3 to 6 carbon atoms, hydroxyaliphenyl of 1 to 4 carbon atoms, alkoxyaliphenyl of 2 to 4 carbon atoms, haloalkoxyalkyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, haloalgenyl of 2 to 4 carbon atoms, alginyl of 3 to 4 carbon atoms, haloalguinyl of 3 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkenynyloxy of 2 to 4 carbon atoms, haloalgenyloxy of 2 to 4 carbon atoms, alkynyloxy of 3 to 4 carbon atoms, haloalkynyloxy of 3 to 4 carbon atoms carbon, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, allylsulfinyl of 1 to 4 carbon atoms, haloalguylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 carbon atoms, alkenylthio - of 2 to 4 carbon atoms, haloalgenylthio of 2 to 4 carbon atoms, alkenylsulfinyl of 2 to 4 carbon atoms, haloguenylsulfinyl of 2 to 4 carbon atoms, alkenylsulfonyl of 2 to 4 carbon atoms carbon, haloalgenylsulfonyl of 2 to 4 carbon atoms, alkenylthio of 3 to 4 carbon atoms, haloalcholinethio of 3 to 4 carbon atoms, alginyl sulfinyl of 3 to 4 carbon atoms, haloalguylsulfinyl of 3 to 4 carbon atoms, alginylsulfonyl of 3 to 4 carbon atoms, haloalkylsulfonyl of 3 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, dialguilamino of 2 to 8 carbon atoms, cycloalkylamino of 3 to 6 carbon atoms, (C 4 -C 6 alkoxy) cycloalbumylamino, C 2 -C 6 -carbonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylaminocarbonyl, dialkylaminocarbonyl with 3 to 8 C atoms of carbon, trialgosilyl having 3 to 6 carbon atoms, phenyl, phenoxy and 5 or 6 membered heteroaromatic rings, each phenyl ring, phenoxy and 5 or 6 membered heteroaromatic ring optionally substituted with one to three substituents which are independently selected from R45; or two adjacent R7, taken together as -0CH0-, CH2CH20-, -OCH (CH3) 0-, -0C (CH3) 20-, -0CF20-, -CF2CF20-, OCF2CF20- or -CH = CH-CH = CH -; R15 is H, halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms or alkylcarbonyloxy of 2 to 4 carbon atoms; R16 is H, halogen, alkenyl of 1 to 4 carbon atoms or haloalguile of 1 to 4 carbon atoms; or R15 and R16 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; R20 is H, alkyl of 1 to 4 carbon atoms or haloalguyl of 1 to 3 carbon atoms; R21 is H, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 3 carbon atoms; R22 and R23 are independently H or alkyl of 1 to 4 carbon atoms; R 24 is H, C 1-4 alkoxy optionally substituted with 1-2 of R 30, alkenyl of 2 to 4 carbon atoms optionally substituted with 1-2 of R 31 or alkinyl of 2 to 4 carbon atoms optionally substituted with 1 -2 of R32; or R24 is C (= 0) R33, nitro, OR34, S (0) 2R35, N (R36) R37 or N = C (R62) R63; R25 is H, alkyl of 1 to 4 carbon atoms optionally substituted with 1-2 of R30 or C (= 0) R33; or R24 and R25 are taken together as a radical which is selected from - (CH2) 4-, - (CH2) 5-. -CH2CH = CHCH2- y. (CH2) 20 (CH2) 2-, each radical is optionally substituted with 1-2 of R38; or R24 and R25 are taken together as = C (R39) N (R40) R41 or = C (R42) OR43; each R, R and R is independently halogen, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 carbon atoms, haloalkylthio of 1 to 3 carbon atoms, amino, alkylamino of 1 to 3 carbon atoms, dialkylamino of 2 to 4 carbon atoms or alkoxycarbonyl of 2 to 4 carbon atoms; each R33 is independently H, alkyl of 1 to 14 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy or benzyloxy; R34 is H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms or CHR66C (O) OR67; R 35 is alkenyl of 1 to 4 carbon atoms or haloalguile of 1 to 3 carbon atoms; R36 is H, alkyl of 1 to 4 carbon atoms or C (= 0) R64; R is H or alkenyl of 1 to 4 carbon atoms; each R38 is independently halogen, alkenyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 carbon atoms, haloalkylthio of 1 to 3 carbon atoms , amino, alkylamino of 1 to 3 carbon atoms, dialkylamino of 2 to 4 carbon atoms or alkoxycarbonyl of 2 to 4 carbon atoms; R39 is H or alkyl of 1 to 4 carbon atoms; R40 and R41 are independently H or alkenyl of 1 to 4 carbon atoms; or R40 and R41 are taken together as - (CH2) 4-, - (CH2) 5-, -CH2CH = CHCH2- or - (CH2) 20 (CH2) -; R42 is H or alkenyl of 1 to 4 carbon atoms; R43 is alkenyl of 1 to 4 carbon atoms; each R45 is independently halogen, cyano, nitro, alkoyl of 1 to 4 carbon atoms, haloalguilo of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halocycloalkyl of 3 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, haloalkynyl of 3 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio 1 to 4 carbon atoms, haloalkylthio, of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, dialkylamino of 2 to 8 atoms carbon, cycloalkylamino of 3 to 6 carbon atoms, (alyl) cycloalkylamino of 4 to 6 carbon atoms, carbonylcarbonyl of 2 to 4 carbon atoms, alkoxycarbonyl of 2 to 6 carbon atoms, alkylaminocarbonyl of 2 to 6 carbon atoms diallylaminocarbonyl of 3 to 8 carbon atoms or trialkylsilyl of 3 to 6 carbon atoms; R62 is H, alkenyl of 1 to 4 carbon atoms or phenyl optionally substituted with 1-3 of R65; R63 is H or alkenyl of 1 to 4 carbon atoms; or R62 and R63 are taken together as - (CH2) - or - (CH2) 5-; R64 is H, alkoyl of 1 to 14 carbon atoms, haloalguile of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy or benzyloxy; each R65 is independently CH3, Cl or OCH3; R66 is H, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; R67 is H, alkenyl of 1 to 4 carbon atoms or benzyl; j is 0 or 1; and k is 0 or 1; with the proviso that: (a) when K is 0, then j is 0; (b) when R2 is CH2ORa then R is optionally substituted H, allyl or benzyl, then R3 is different from cyano; (c) when R1 is phenyl substituted by Cl in each of the meta positions, the phenyl is also substituted by R7 in the para position; (d) when R1 is phenyl substituted by R7 in the para position and R7 is different from terbutyl, cyano or optionally substituted phenyl; (e) when R1 is cyclopropyl or isopropyl optionally with 1-5 of R6, then R is different from C (= W) N (Rb) S (0) 2-Rc-Rd where W is 0, S, NRe or N0Re; Rb is hydrogen, alkenyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkinyl of 2 to 6 carbon atoms; Rc is a direct link or CHRf, 0, NRe or N0Re; Rd is an optionally substituted aromatic carbocyclic or heterocyclic radical having 5 to 6 ring atoms, the radical optionally being condensed with an aromatic or non-aromatic 5 or 6 membered ring; each Re is independently H, alkenyl of 1 to 3 carbon atoms, haloalguile of 1 to 3 carbon atoms or phenyl; Rf is H, alkyl of 1 to 3 carbon atoms or phenyl; and (f) the compound of formula I is different from diethyl 6-amino-5-nitro-2-phenyl-4-pyrimidinomalonate. More particularly, this invention pertains to a compound of formula I, which includes all geometric isomers and stereoisomers, N-oxides or agriculturally suitable salts thereof. This invention also relates to a herbicidal composition comprising a herbicidally effective amount of a compound of formula I and at least one of a surfactant, a solid diluent or a liquid diluent. This invention is further related to a method for eliminating unwanted vegetation growth which comprises contacting the vegetation to its environment with a herbicidally effective amount of a compound of formula I (for example as a composition described herein). This invention also relates to a herbicidal mixture comprising a herbicidally effective amount of a compound of formula I and an effective amount of at least one additional active ingredient which is selected from the group consisting of another herbicide and a herbicide sanitizer. The invention further relates to a herbicidal composition comprising a herbicidally effective amount of a compound of formula I, an effective amount of at least one additional active ingredient which is selected from the group consisting of another herbicide and a herbicide sanitizer, and at least one of a surfactant, a solid diluent or a liquefied diluent.
DETAILED DESCRIPTION OF THE INVENTION As used herein, the terms "comprising", "included", "which includes", "included", "which has", "which is contained" or any other variation thereof, are For example, a composition, procedure, method, article or apparatus that comprises a list of elements is not necessarily limited to only those elements but may also include other elements that are not expressly included or inherent in said composition, method, method, article or apparatus Furthermore, unless stated otherwise, "or" refers to an inclusive or not to an exclusionary, for example, a condition A or B is satisfied by any of the following: A is valid (or is present) and B is false (or is not present), A is false (or is not present) and B is valid (or is present), both A and B are valid (or are In addition, the indefinite articles "a" and "an" which precede an element or component of the invention are intended not to be restrictive with respect to the number of instances (i.e., presentations) of the element or component. Therefore, the terms "a", or "one" should be considered to include one or at least one, and that the singular wording of the element or component also includes the plurality, unless the number evidently means singular.
In what is described above, the term "alkyl" is used alone or in compound words such as "alkylthio" or "haloalkyl" includes straight or branched chain alkyl such as methyl, ethyl, n-propyl, i-propyl or different butyl, pentyl or hexyl isomers. The term "alkenyl" includes straight or branched chain alkenes such as ethenyl, 1-propenyl, 2-propenyl and the different isomers of butenyl, pentenyl and hexenyl. The term "alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. The term "alkynyl" includes straight or branched chain alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. The term "alguinyl" also includes portions consisting of multiple triple bonds such as 2,5-hexadiinyl. The term "alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different isomers of butoxy, pentoxyl and hexyloxy. The term "alkoxyalipyl" denotes alkoxy substitutions in algae. Examples of "alkoxyalipyl" include CH30CH2, CH3OCH2CH2, CH3CH20CH2 and CH3CH0CH2CH2. The term "alkenyloxy" includes alkennyloxy portions of straight or branched chain. Examples of "alkenyloxy" include H2C = CHCH20, (CH3) CH = CHCH20 and CH2 = CHCH2CH2o. The term "alkynyloxy" includes straight or branched alynyloxy portions. Examples of "alkynyloxy" include HC = CCH20 and CH3C = CCH20. The term "alguiltium" includes branched or straight chain alkylthio portions such as methylthio, ethylthio and the different isomers of propylthio and butylthio. The term "alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "allylsulfyl" include CH3S (0), CH3CH2S (0), CH3CH2CH2S (0), (CH3) 2CHS (0) and the different butyl sulfyl isomers. Examples of "alkylsulfonyl" include CH3S (0) 2 / CH CH2S (0) 2 CH3CH2CH2S (0) 2, (CH3) 2CHS (0) 2 and the different butyl sulfyl isomers. The terms "alkylamino", "di allyl amino", "alkenylthio", "alkenylsulfinyl", alkenylsulfonyl "," alkynylthio ", "alkynylsulfyl", "alkynylsulfonyl" and the like are defined analogously to the previous examples. The term "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of "cycloalguylalguilo" include cyclopropylmethyl, cyclopentylethyl and other cycloalkyl portions attached to straight or branched chain alkenyl group. The term "alkylcycloalyl" denotes alkyl substitution on a cycloalguyl moiety. Examples include 4-methylcyclohexyl and 3-ethylcyclopentyl. The term "heteroaromatic ring" includes fully aromatic heterocycles. Aromatic indicates that each of the atoms in the ring is essentially in the same plane and has a p-orbital perpendicular to the plane of the ring and in which they are associated with the ring to comply with Hückel's rule (4n + 2) electrons p, when n is 0 or a positive integer. The term cyclo-cyclic aromatic radical is synonymous with the term isocitic aromatic radical. A wide variety of synthetic methods are known in the art to allow the preparation of aromatic heterocyclic rings; for extensive reviews see the set of eight volumes of Comprehen if you see He t ero c i c Chemi s try, A. R. Katrotzky and C.. Rees editor in chief, Pergamon Press, Oxford, 1984 and the twelve volumes of Comprehen if he sees He t ero cycli c Chemi s try II, AR Katrotzky, CW Rees and EFV Scriven editor in chief, Pergamon Prees, Oxford, 1996. The rings 5 and 6 membered heteroaromatics described for R7 typically comprise 1 to 4 members in the heteroatom ring, the heteroatom members are selected from 0-4 N atoms, 0-1 O atoms and 0-1 S atoms. Test 1 shows examples of heteroaromatic rings; H-1- to H-55 are considered as illustrative rather than limiting heteroaromatic rings within the scope of the present invention.
Test 1 H-l H-2 H-3 H- H-5 H-6 H-7 H-8 H-9 H-10 H-11 H-12 H-13 H-14 H-15 H-16 H-17 - H-18 H-19 H-20 - H-21 H-22 H-23 H-24 H-25 H-26 H-27 H-29 H-30 H-31 H-32 H-34 H-35 H-36 H-41 H-42 H-43 H-44 H-53 H-54 H-55 where each R is independently R 45;, R71a, R72 and R73 are independently H or R45; p is an integer from 0 to 3; and g is an integer from 0 to 2. References herein to groups R7, H1a refer to those shown in test 1. A person skilled in the art will appreciate that not all heterocycles containing nitrogen can form N-oxides given that a nitrogen is regulated with a pair of electrons only available for oxidation to the oxide; a person skilled in the art will recognize nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. The synthesis methods for the preparation of N-oxides of heterocycles and tertiary amines are well known to those skilled in the art and include the oxidation of heterocycles and tertiary amines with peroxyacids such as peracetic acid and m-chloroperbenzoic acid (MCPBA, for its acronyms), hydrogen peroxide, algeryl hydroperoxide such as tertbutyl hydroperoxide, sodium perborate and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and have been reviewed in the literature, see, for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. Mckillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp. 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press. The term "halogen" only in compound words such as "haloalkyl" includes fluorine, chlorine, bromine or iodine. In addition, when used in compound words such as "haloalkyl", the alkyl may be partially or completely substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F3C, C1CH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalguylthio" and the like are defined analogously to the term "haloalguyl". Examples of "haloalgenyl" include (C1) 2C = CHCH2 and CF3CH2CH = CHCH2. Examples of "haloalguinyl" include HC = CCHCl, CF3C = C, CC13C = C and FCH2C = CCH2. Examples of "haloalkoxy" include CF30, CC13CH20, HCF2CH2CH20 and CF3CH20. Examples of "haloalguiltium" include CC1S, CF3S, CC13CH2S and CICH2CH2CH2S. Examples of "haloalguylsulfinyl" include CF3S (0), CC13S (0), CF3CH2S (0) and CF3CF2S (O). Examples of "haloalbumylsulfonyl" include CF3S (0) 2, CC13S (0) 2 / CF3CH2S (0) 2 and CF3CF2S (0) 2. The total number of carbon atoms in a substituent group is indicated by the prefix of i to j carbon atoms where i and j are numbers from 1 to 14. For example, alkoxylsulfonyl of 1 to 3 carbon atoms denotes from -methylisulfonyl to propylsulfonyl; C2-alkoxyaliphenyl indicates CH30CH2; C 3 -alkoxyaliphenyl indicates, for example, CH 3 CH (OCH 3), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2; and C 4 -alkoxyalipyl indicates the various isomers of an alkoyl group substituted with an alkoxy group containing a total of 4 carbon atoms, examples include CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2. Examples of "alkylcarbonyl" include C (0) CH3, C (0) CH2CH2CH3 and C (0) CH (CH3) 2. Examples of "alkoxycarbonyl" include CH30C (= 0), CH3CH2OC (= 0), CH3CH2CH2OC (= 0), (CH3) 2CH0C (= 0) and the different butoxy- or pentoxycarbonyl isomers. In what is described above, when a compound of formula I is composed of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by substitution of a hydrogen on carbon or nitrogen. When a compound is substituted with a substituent having a subscript (eg (Rd)? - 3) it indicates the number of times (ie, of presentations) that said substituent may vary or the substituent is preceded by a numerical range ( for example 1-3 Rd) indicates that the number of instances of said substituent may vary, then when the number of said instances is greater than 1, each instance is independently selected from the group of radicals defined for the substituent. Further, when the subscript indicates a range, for example (Rd) i-j, then the number of substituting instances may be selected from the integers between i and j, inclusive. The term "-CH-fC (0) 0 (CH2) a4-" means The term "-CH-O (CH2) nY 'means O (CH2) H When a group contains a substituent which may be hydrogen, for example R15 or R34, then this substituent is taken as hydrogen, and it is recognized that it is eguivalent that said group be unsubstituted. The compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereoisomers, atropisomers and geometric isomers. A person skilled in the art will appreciate that a stereoisomer may be more active and / or may have beneficial effects when its concentration increases relative to one or more other stereoisomers or when it is separated from one or more additional stereoisomers. Additionally, a person skilled in the art knows how to separate, increase the concentration and / or selectively prepare said stereoisomers. Accordingly, the present invention comprises compounds selected from formula I, N-oxides and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or an optically active form. The compounds of formula I wherein R is C02H (ie, a carboxylic acid function) are considered to be compounds that bind to an active site in a plant enzyme or a receptor that causes a herbicidal effect on the plant. Other compounds of formula I wherein the R substituent is a group which can be transformed into plants or the environment into a carboxylic acid function (ie, C02H) which provides similar herbicidal effects and is within the scope of the present invention. Therefore, "a herbicidally effective derivative of CO2H", when used to describe the substituent R in formula I is defined as any salt, ester, carboxamide, acyl hydrazide, imidate, thioimidate, amidine, acyl halide, acyl cyanide. , acid anhydride, ether, acetal, orthoester, carboxaldehyde, oxime, hydrazone, thioacid, thioester, dithiolyester, nitrile or any other carboxylic acid derivative known in the art which does not suppress the herbicidal activity of the compound of formula I and is or can be hydrolyzed, oxidized, reduced or metabolized in some other way in plants or in soil to provide the function of carboxylic acid, which depends on the pH, whether in its dissociated or non-dissociated form. Agriculturally suitable salts of the compounds of the invention are salts formed by contact with acids or bases or through ion exchange such that the salts derived retain sufficient water solubility for bioavailability and therefore herbicidal efficacy and wherein the counterions of the Salts are suitable for use in agriculture. Agriculturally suitable salts of the compounds of the invention include acid addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic acids. , salicylic, tartaric, 4-toluenesulfonic or valeric. Agriculturally suitable salts of the compounds of the invention also include aguellas formed with strong bases (for example sodium, potassium, lithium or quaternary ammonium hydroxide) or amines. A person skilled in the art recognizes that due to the environment and under the physiological conditions, the salts of the compounds of the invention are in equilibrium with their corresponding forms which are not salts, the agriculturally suitable salts share the biological utility of the forms they are not salts.
Particularly useful are the agriculturally suitable salts of the compounds of formula I wherein R is CO2H (which include wherein R2 is CO2H) formed with strong bases or amines. As is well known in the art, the contact of a carboxylic acid (CO2H) group with a base causes deprotonation to provide the corresponding carboxylate ion (C02) and a typically positively charged counterion derived from the base. A wide range of counterions form the agriculturally suitable salts of the compounds of formula I, wherein R is CO2H, since most of the derived salts have sufficient water solubility for bioavailability. Illustrative and particularly noteworthy are the salts of compounds of formula I and which R is C02H wherein the counterion is an alkali metal cation such as lithium, sodium or potassium, quaternary ammonium such as tetramethylammonium, ternary sulfonium such as trimethylsulfonium or derivative of an amine such as dimethylamine, diethanolamine (diolamine), triethanolamine (trolamine). Also particularly useful are the ester and thioester derivatives of CO 2 H as R in the compounds of formula I. As is well known in the art, the ester groups (ie, C 2 RAL) result from the condensation of a carboxylic acid function ( C02H) with an alcohol (ie, RAL0H) where RAL is radical derived from alcohol; A wide variety of methods are known for preparing said esters. Analogously, the thioester groups of formula C (0) SRAL can be conceptually visualized as the condensation product of a carboxylic acid function with a thioalcohol (often referred to as a mercaptan) of the formula RALSH; A variety of methods for preparing such thioesters are known. As compounds of formula I, wherein R is C02H which are herbicidally active and their esters and thioesters derivatives are susceptible to hydrolysis (where R is CO2H) particularly in the presence of hydrolytic enzymes, the compounds of formula I wherein R1 is an ester (ie, C02RAL) or thioester (ie, C (0) SRAL) are generally useful as herbicides. Of the herbicidally effective derivatives of CO2H, the ester and thioester derivatives, particularly the ester derivatives, are among the most convenient and useful preparations. If the RAL radical has more than one OH or SH function, the radical can then be condensed with more than one pyrimidine ring system of formula I having CO2H as R. As the derivatized derivatives of multiple derivatives can be hydrolyzed to the compound of I formula having CO2H as R, said multiplicity of esterified derivatives are among the herbicidally effective derivatives of C02H. Illustrative and noteworthy are the ester and thioester compounds of formula I in which R is C02H which is esterified with methanol, ethanol, butanol, 2-butoxyethanol, 2-ethylhexanol, isopropanol, 2-methylpropanol (isobutanol), octanol isomers ( isoctanol) and ethanethiol to form esters of methyl, ethyl, butyl, 2-butoxyethyl, 2-ethylhexyl, isopropyl, 2-methylpropyl, -5-isoctyl and ethylthio, respectively. Particularly noteworthy are the methyl and ethyl esters. The embodiments of the present invention include: Modality 1. A compound of formula I wherein j is 0. 10 Modality 2. A compound of formula I wherein k is 0 Modality 3. A compound of formula I wherein R 15 is H Modality 4. A compound of modality 3, where RAL is H. Mode 5. A compound of formula I wherein: R is C02R12, CH20R13, CH (OR46) (OR47), CHO, C (= NOR14) H, C (= NNR48R49) H, C (= 0 ) N (R18) R19, C (= S) OR50, C (= 0) SR51, C (= S) SR52 or C (= NR53) YR54; R12 is H, -CH-tC (0) 0 (CH2) mY -N = C (R55) 56; or a radical which is selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alkylcycloalkyl of 4 to 12 carbon atoms, cycloalkylguanyl of 4 to 12 carbon atoms, alkenyl of 2 to 14 carbon atoms. carbon, 25 alginyl of 2 to 14 carbon atoms and phenyl, each radical is optionally substituted with 1-3 of R27; or R12 is a divalent radical that joins the carboxyl ester function C02R12 of each two pyrimidine ring systems of formula I, the divalent radical is selected from -CH2-, - (CH2) 2-, - (CH2) 3- and - CH (CH3) CH2-; R 13 is H, alkenyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R 28 or benzyl; R 14 is H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms or benzyl; R18 is H, alkyl of 1 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms or S (0) 2R57; R19 is H or alkyl of 1 to 4 carbon atoms; each R27 is independently halogen, cyano, hydroxycarbonyl, alkoxycarbonyl of 2 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alguiltium of 1 to 4 carbon atoms, haloalguiltium of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 carbon atoms, dialguilamino of 2 to 4 carbon atoms, -CH-f-0 (CH2) p ^ - or phenyl optionally substituted with 1-3 of R44; or two of R27 are taken together as -0C (0) 0- or -0 (C (R58) (R58))? -20-; or two of R27 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R28 is independently halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 atoms of carbon or dialkylamino of 2 to 4 carbon atoms; or two of R28 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R44 is independently halogen, alkoyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 atoms of carbon, haloalkylthio of 1 to 3 carbon atoms, amino, alkylamino of 1 to 3 carbon atoms, dialguilamino of 2 to 4 carbon atoms or nitro; R46 and R47 are independently alkenyl of 1 to 4 carbon atoms or haloalguilo of 1 to 3 carbon atoms; or R4d and R47 are taken together as -CH2CH2-, -CH2CH (CH3) -o YCH2) 3-; R48 is H, alkyl of 1 to 4 carbon atoms, haloalguyl of 1 to 4 carbon atoms, carbonylcarbonyl of 2 to 4 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms or benzyl; R49 is H, alkenyl of 1 to 4 carbon atoms or haloalguile of 1 to 4 carbon atoms; R, R and R are H; or a radical which is selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alkylcycloalguyl of 4 to 12 carbon atoms, cycloalguilaylguile of 4 to 12 carbon atoms, alkenyl of 2 to 14 carbon atoms. carbon and alginyl of 2 to 14 carbon atoms, each radical is optionally substituted with 1-3 of R27; And it is 0, S or NR61; R53 is H, alkenyl of 1 to 3 carbon atoms, haloalguile of 1 to 3 carbon atoms, alkoxyalguile of 2 to 4 carbon atoms, OH or alkoxy of 1 to 3 carbon atoms; R54 is alkenyl of 1 to 3 carbon atoms, haloalguile of 1 to 3 carbon atoms' or alkoxyaliphenyl of 2 to 4 carbon atoms; or R53 and R54 are taken together as - (CH2) 2-, -CH2CH (CH3) - or - (CH2) 3-; R55 and R56 are independently alkenyl of 1 to 4 carbon atoms; R57 is alkenyl of 1 to 4 carbon atoms, haloalguile of 1 to 3 carbon atoms or NR59R60; each R58 is independently selected from H and alkyl from 1 to 4 carbon atoms; R59 and R60 are independently H or alkenyl of 1 to 4 carbon atoms; R61 is H, alkenyl of 1 to 3 carbon atoms, haloalguilo of 1 to 3 carbon atoms or alkoxyalguilo of 2 to 4 carbon atoms; m is an integer from 2 to 3; and n is an integer from 1 to 4. Modality 6. A compound of formula I, wherein, when R1 is optionally substituted cyclopropyl, then R2 is different from alkoxyalkenyl or allylthioalguyl. Modality 7. A compound of formula I, wherein R2 is different from alkoxyaluyl or allylthioalguyl. Modality 8. A compound of mode 5, wherein: R2 is C02R12, CH20R13, CH (OR46) (OR47), CHO, C (= N0R14) H, C (= NNR48R49) H, (O) C (R15) ( R16) C02R17, C (= 0) N (R18) R19, C (= S) 0R50, C (= 0) SR51, C (= S) SR52 or C (= NR53) YR54; R17 is alkenyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R29 or benzyl; and each R29 is independently halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alguiltio of 1 to 4 carbon atoms, haloalguiltio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 carbon atoms or dialguilamino of 2 to 4 carbon atoms. Modality 9. A compound of mode 8, wherein, when R2 is CH20R13, then R13 is different from alguil. Modality 10. A compound of mode 8, wherein when R2 is CH20R13, then R13 is different from optionally substituted alger. Mode 11. A compound of mode 8, wherein R2 is different from CH2OR13. Mode 12. A compound of mode 8, wherein j is 0. Mode 13. A compound of mode 12, wherein R2 is C02R12, CH2OR13, CHO or CH2C02R17. Modality 14. A compound of mode 13, "wherein R2 is C02R12 'Mode 15. A compound of mode 14, wherein R12 is H, alkenyl of 1 to 8 carbon atoms or alkenyl of 1 carbon atom substituted with phenyl optionally substituted with 1-3 of R44 Modality 16. A compound of mode 15, wherein R12 is H, alkenyl of 1 to 4 carbon atoms or alkenyl of 1 carbon atom substituted with phenyl optionally substituted with 1-3 of R44. Modality 17. A compound of mode 16, wherein R12 is H, alkoyl of 1 to 4 carbon atoms or benzyl, Modality 18. A compound of formula I, wherein R2 is C02H, an agriculturally suitable salt or an ester or thioester derivative thereof. Modality 19. A compound of mode 18, wherein R2 is C02H, a suitable agricultural salt or an ester derivative thereof.
Modality 20. A compound of formula I, wherein R 1 is cyclopropyl optionally substituted with 1-5 of R 5. Modality 21. A compound of formula I, wherein R 1 is isopropyl optionally substituted with 1-5 of R 6. Modality 22. A compound of formula I wherein R 1 is phenyl optionally substituted with 1-3 of R 7. Modality 23. A compound of formula I, wherein R 1 is cyclopropyl optionally substituted with 1-5 of R 5 or isopropyl optionally substituted with 1-5 of R 6. Mode 24. A compound of formula I, wherein R1 is cyclopropyl optionally substituted with 1-5 of R5 or phenyl optionally substituted with 1-3 of R7. Modality 25. A compound of formula I, wherein R 1 is isopropyl optionally substituted with 1-5 of R 6 or phenyl optionally substituted with 1-3 of R 7. Modality 26. A compound of formula I, wherein R 1 is different from cyclopropyl. Modality 27. A compound of formula I, wherein R 1 is cyclopropyl optionally substituted with 1-2 of R 6 or phenyl optionally substituted with 1-3 of R 7. Modality 28. A compound of mode 27, wherein R 1 is cyclopropyl optionally substituted with 1-2 of R 6. Mode 29. A compound of mode 27, wherein R 1 is cyclopropyl or phenyl optionally substituted with 1-3 of R 7. Mode 30. A compound of mode 28, wherein R 1 is cyclopropyl. Mode 31. A compound of mode 27, wherein R 1 is phenyl optionally substituted with 1-3 of R 7. Modality 32. A compound of mode 27, wherein R1 is cyclopropyl or phenyl optionally substituted with a radical R7 in the para position and optionally with 1-2 of R7 in other positions. Modality 33. A compound of mode 32, wherein R 1 is cyclopropyl or phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals which are selected from halogen and methyl in other positions. Mode 34. A compound of the mode 33, wherein R 1 is cyclopropyl or phenyl substituted with a halogen radical in the para position and optionally with 1-2 radicals which are selected from halogen and methyl in other positions. Modality 35. A compound of mode 34, wherein R 1 is cyclopropyl or phenyl substituted with a radical Br or Cl in the para position and optionally with 1-2 radicals which are selected from halogen and methyl in the other positions. Modality 36. A compound of mode 35, wherein R1 is phenyl substituted with a radical Br or Cl in the para position and optionally with 1-2 radicals which are selected from halogen and methyl in other positions. Modality 37. A compound of the mode 35, wherein R 1 is cyclopropyl or phenyl substituted with a radical Br or Cl in the para position. Mode 38. A compound of the embodiment 37, wherein R 1 is phenyl substituted with a radical Br or Cl in the para position. Modality 39. A compound of formula I, wherein R7 is different from cyano. Modality 40. A compound of formula I, wherein R7 is selected from another of optionally substituted phenyl, phenoxy and 5- and 6-membered heteroaromatic rings. Modality 41. A compound of formula I, wherein each R7 is independently selected from halogen, alkoyl of 1 to 2 carbon atoms, haloalguile of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms or haloalkoxy of 1 to 2 carbon atoms; or two adjacent R7 are taken together as -0CH20-, -CH2CH20-, -OCH (CH3) 0-, -OC (CH3) 20-, -0CF20-, -CF2CF20-, -OCF2CF20- or -CH = CH-CH = CH-. Modality 42. A compound of mode 41, wherein each R7 is independently selected from halogen, alkoyl of 1 to 2 carbon atoms, haloalguile of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms or haloalkoxy of 1 to 2 carbon atoms; or two adjacent R7 are together as: -0CH20-, -CH2CH20-, -OCH (CH3) 0- or -0CF20-. Modality 43. A compound of embodiment 42, wherein each R7 is independently selected from halogen, alkenyl of 1 to 2 carbon atoms, fluoroalguile of 1 carbon atom, alkoxy of 1 to 2 carbon atoms or fluoroalkoxy of 1 carbon atom. Modality 44. A compound of formula I, wherein each R7 is independently selected from halogen, methyl and methoxy. Modality 45. A compound of mode 44, wherein each R7 is independently selected from halogen and methyl. Modality 46. A compound of mode 45, wherein each R7 is independently selected from F, Cl and Br. Modality 47. A compound of modality 46, wherein each R7 is independently selected from Cl and Br. Modality 48. A compound of Formula I, where R3 is different from cyano. Modality 49. A compound of formula I, wherein R3 is different from nitro. Modality 50. A compound of formula I, wherein R3 is halogen, nitro, OR20, SR21 or N (R22) R23. Modality 51. A compound of mode 50, wherein R3 is halogen.
Modality 52. A compound of mode 51, wherein R3 is Br or Cl. Modality 53. A compound of mode 52, where R3 is Cl. Modality 54. A compound of formula I, wherein R4 is -N (R2) R25. Modality 55. A compound of formula I, wherein R4 is different from alginyl of 2 to 4 carbon atoms optionally substituted with 1-2 of R32. Modality 56. A compound of formula I, wherein R24 is H, C (0) R33 or alkyl of 1 to 4 carbon atoms optionally substituted with R30; R25 is H or alkyl of 1 to 2 carbon atoms; or R24 and R25 are taken together as = C (R39) N (R40) R41. Modality 57. A compound of the embodiment 56, wherein R24 is H, C (O) CH or alkenyl of 1 to 4 carbon atoms optionally substituted with R30; and R25 is H or alkenyl of 1 to 2 carbon atoms. Modality 58. A compound of mode 57, wherein R 24 and R 25 are independently H or methyl. Modality 59. A compound of embodiment 58, wherein R24 and R25 are H. Modality 60. A compound of formula I, wherein R30 is halogen, methoxy, fluoroalkoxy of 1 carbon atom, methylthio, fluoroalguiltio of 1 carbon atom, amino, methylamino, dimethylamino or methoxycarbonyl. Modality 61. A compound of formula I, wherein R33 is H or alkenyl of 1 to 3 carbon atoms. Modality 62. A compound of mode 61, wherein R33 is CH3. Modality 63. A compound of formula I, wherein R39 is H or alkyl of 1 to 2 carbon atoms. Modality 64. A compound of formula I, wherein R40 and R41 are independently H or alkenyl of 1 to 2 carbon atoms. Modality 65. A compound of formula I, wherein R3 is different from OH. Modality 66. A compound of formula I, wherein R3 is different from OR20. Modality 67. A compound of formula I, wherein, j is 1 and R1 is isopropyl substituted with at least one of R6 which is halogen, then R24 and R25 are each H. Modality 68. A compound of formula I, in where, when j is 1, R1 is optionally substituted isopropyl, and R24 and R25 are each H. Modality 69. A compound of formula I, wherein, when j is 1, then R24 and R25 are each H. Modality 70 A compound of formula I, wherein, when j is 1, then R6 is different from halogen. Modality 71. A compound of formula I, wherein, when j is 1, then R1 is different from optionally substituted isopropyl. Modality 72. A compound of formula I, wherein, when j is 1, then R 1 is cyclopropyl optionally substituted with 1-5 of R 5, isopropyl or phenyl optionally substituted with 1-3 of R 7. Modality 73. A compound of formula I, wherein, when j is 1, then R1 is cyclopropyl, isopropyl or phenyl optionally substituted with 1-3 of R7. Modality 74. A compound of formula I wherein, when R1 is phenyl optionally substituted with 1-3 of R7, then R is different from cyano. Modality 75. A compound of formula I wherein R is different from cyano. Modality 76. A compound of mode 5, wherein, when R1 is phenyl optionally substituted with 1-3 of R7, then R is C02R12. Modality 77. A compound of mode 5, where R is C02R12. Modality 78. A compound of mode 8 wherein, when R1 is phenyl optionally substituted with 1-3 of R7, then R2 is C02R12. Modality 79. A compound of mode 8, where R2 is C02R12. Modality 80. A compound of formula I, wherein, when R1 is phenyl optionally substituted with 1-3 of R7, then R24 is H, C (= 0) R33, nitro, OR34, S (0) 2R35 or N (R36 ) R37, and R25 is H or C (= 0) R33. Modality 81. A compound of formula I, wherein, wherein R1 is phenyl optionally substituted with 1-3 of R7, then R24 and R25 are each H. Modality 82. A compound of formula I, wherein R24 is H, C (= 0) R33, nitro, OR34, S (0) 2R35 or N (R36) R37, and R25 is H or C (= 0) R33. Modality 83. A compound of formula I, wherein R 24 and R 25 are each H. Modality 84. A compound of formula I, wherein, when R 1 is cyclopropyl or isopropyl optionally substituted with 1-5 of R 6, then R is different from C (= W 1) N (R 1) S (0) 2-Rcd wherein W comprises at least one atom; Rbl comprises at least one atom and Rcd comprises at least one atom. Modality 85. A compound of formula I, wherein, when R1 is cyclopropyl optionally substituted with 1-5 of R5 or isopropyl optionally substituted with 1-5 of R6, then R is different from C (= WX) N (Rbl) S (O) 2-Rcd wherein W comprises at least one atom; Rbl comprises at least one atom and Rcd comprises at least one atom. Modality 86. A compound of formula I, wherein, R is different from C (= WX) N (Rbl) S (O) 2-Rcd wherein W comprises at least one atom; Rbl comprises at least one atom and Rcd comprises at least one atom. Modality 87. A compound of mode 5, wherein R18 is H, alkoyl of 1 to 4 carbon atoms, hydroxy or alkoxy of 1 to 4 carbon atoms. Modality 88. A compound of mode 8, wherein R18 is H, alkyl of 1 to 4 carbon atoms, hydroxy or alkoxy of 1 to 4 carbon atoms. Modality 89. A compound of formula I, wherein each R5 and R6 is independently halogen, alkenyl of 1 to 2 carbon atoms or haloalkyl of 1 to 2 carbon atoms. Modality 90. A compound of formula I, wherein R15 is H, halogen, alkoyl of 1 to 4 carbon atoms, haloalguile of 1 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms or alkoylcarbonyloxy of 2 to 4 carbon atoms. Modality 91. A compound of formula I, wherein R16 is H, halogen, alkenyl of 1 to 4 carbon atoms or haloalguilo of 1 to 4 carbon atoms. Modality 92. A compound of formula I, wherein R24 is H, alkyl of 1 to 4 carbon atoms optionally substituted with 1-2 of R30, alkenyl of 2 to 4 carbon atoms optionally substituted with 1-2 of R31 or alternatively of 2 to 4 carbon atoms optionally substituted with 1-2 of R32; or R24 is C (= 0) R33, nitro, OR34, S (0) 2R35 or N (R36) R37.
Modality 93. A compound of formula I, wherein each R33 is independently H, alkoyl of 1 to 4 carbon atoms, haloalguile of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenoxy or benzyloxy. Modality 94. A compound of formula I, wherein R34 is H, alkyl of 1 to 4 carbon atoms or haloalguile of 1 to 3 carbon atoms. Modality 95. A compound of formula I, wherein R36 is H or alkenyl of 1 to 4 carbon atoms. Modality 96. A compound of mode 5, wherein R12 is H; or a radical which is selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alkylcycloalguyl of 4 to 12 carbon atoms, cycloalguilaylguile of 4 to 12 carbon atoms, alkenyl of 2 to 14 carbon atoms. carbon and alginyl of 2 to 14 carbon atoms, each radical optionally being substituted with 1-3 of R27; or N = C (R55) R56. Modality 97. A compound of mode 5, wherein each R27 is independently halogen, hydroxycarbonyl, alkoxycarbonyl of 2 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio from 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 carbon atoms, dialguilamino of 2 to 4 carbon atoms, -CH-O (CH2) Y or optionally substituted phenyl with 1 - 3 of R; or two of R are taken together as -0C (0) 0- or -0 (C (R58) (R58))? -20-; or two of R27 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety. Modality 98. A compound of mode 5, wherein R53 is H, alkyl of 1 to 3 atoms. of carbon, haloalkyl of 1 to 3 carbon atoms or alkoxyalkyl of 2 to 4 carbon atoms. The combinations of embodiments 1-98 are illustrated by: Modality A. A compound of formula I, wherein: R2 is C02R12, CH20R13, CH (OR46) (OR47), CHO, C (= N0R14) H, (O) jC (R15) (R16) C02R17, C (= NNR48R49) H, C (= 0) N (R18) R19, C (= S) OR50, C (= 0) SR51, CYS) SR52 or C (= NR53) YR54; R12 is H, -CH + C (0) 0 (CH2) m -3, -N = C (R55) 56; or a radical selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alkylcycloalguyl of 4 to 12 carbon atoms, cycloalguilaylguile of 4 to 12 carbon atoms, alkenyl of 2 to 14 carbon atoms. carbon, albinyl of 2 to 14 carbon atoms and phenyl, each radical is optionally substituted with 1-3 of R27; or R12 is a divalent radical joining the carboxyl ester function C02R12 of each of two pyrimidine ring systems of formula I, the divalent radical is selected from -CH2-, - (CH2) 2- / YCH2) 3- and -CH (CH3) CH2-; R 13 is H, alkenyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R 28 or benzyl; R 14 is H, alkyl of 1 to 4 carbon atoms, haloalguyl of 1 to 4 carbon atoms or benzyl; R17 is alkenyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R29, or benzyl; R18 is H, alkyl of 1 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms or S (0) 2R57; R19 is H or alkenyl of 1 to 4 carbon atoms; each R27 is independently halogen, cyano, hydroxycarbonyl, alkoxycarbonyl of 2 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 carbon atoms, dialkylamino of 2 to 4 carbon atoms, -CH-O (CH2) __-_- or phenyl optionally substituted with 1-3 of R44; or two of R27 are taken together as -OC (0) 0- or -0 (C (R58) (R58))? -20-; or two of R27 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R28 is independently halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 atoms carbon or diallylamino of 2 to 4 carbon atoms; or two of R28 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R29 is independently halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 atoms of carbon or dialkylamino of 2 to 4 carbon atoms; each R44 is independently halogen, alkyl of 1 to 4 carbon atoms, haloalguile of 1 to 3 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 atoms of carbon, haloalguiltium of 1 to 3 carbon atoms, amino, alkylamino of 1 to 3 carbon atoms, dialguilamino of 2 to 4 carbon atoms or nitro; R46 and R47 are independently alkenyl of 1 to 4 carbon atoms or haloalguilo of 1 to 3 carbon atoms; or R46 and R47 are taken as -CH2CH2-, -CH2CH (CH3) -o- (CH2.3-, R48 is H, alkoyl with 1 to 4 carbon atoms, haloalguile with 1 to 4 carbon atoms, alkenylcarbonyl from 2 to 4 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms or benzyl; R49 is H, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms; R50, R51 and R52 are H; or a radical selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alylcycloalguyl of 4 to 12 carbon atoms, cycloalguilalguilo of 4 to 12 carbon atoms, alkenyl of 2 to 14 carbon atoms. carbon and alginyl of 2 to 14 carbon atoms, each radical is optionally substituted with 1-3 of R27; And it is 0, S or NR61; R53 is H, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxyaliphenyl of 2 to 4 carbon atoms, OH or alkoxy of 1 to 3 carbon atoms; R54 is alkenyl of 1 to 3 carbon atoms, haloalguile of 1 to 3 carbon atoms or alkoxyalkyl of 2 to 4 carbon atoms; or R53 and R54 are taken together as - (CH2) 2-, -CH2CH (CH3) - or - (CH2) 3-; R55 and R56 are independently alkyl of 1 to 4 carbon atoms; R57 is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms or NR59R60; each R58 is independently selected from H and alkyl of 1 to 4 carbon atoms; R59 and R60 are independently H or alkyl of 1 to 4 carbon atoms; R61 is H, alkyl of 1 to 3 carbon atoms, haloalguile of 1 to 3 carbon atoms or alkoxyalguile of 2 to 4 carbon atoms; m is an integer from 2 to 3; and n is an integer from 1 to 4. Mode B. A mode A compound, wherein R3 is halogen. Mode C. A compound of mode B, wherein R 1 is cyclopropyl or phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals which are selected from halogen and methyl in other positions; and R4 is -N (R24) R25. Mode D. A compound of mode C, wherein R2 is C02R12, CH2OR13, CHO or CH2C02R17. Modality E. A compound of modality D, where R24 is H, C (0) R33 or alkenyl of 1 to 4 carbon atoms optionally substituted with R30; R25 is H or alkenyl of 1 to 2 carbon atoms; or R24 and R25 are taken together as = C (R39) N (R40) R41. Mode F. A compound of mode E, wherein R2 is C02R12; and R24 and R25 are H. Modality G. An F-modal compound, wherein R12 is H, alkyl of 1 to 4 carbon atoms or benzyl. Specific embodiments include compounds of formula I which are selected from the group consisting of: methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidine carboxylate, 6-amino-5-brorno-2-cyclopropyl-4 -ethyl pyrimidine-carboxylate, phenylmethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidine-carboxylate, 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt, 6-amino Methyl-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylate, phenylmethyl 6-amino-5-chloro-2-cyclopropyl-pyrimidine-carboxylate, monosodic salt of 6-amino-5-chloro-2-acid cyclopropyl-4-pyrimidinecarboxylic acid, 6-amino-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylate, methyl 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidinecarboxylate, Ethyl 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylate, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylic acid, 6-amino -2- (4-bromophenyl) -5-chloro-4-pyrimidine-carboxylic acid ethyl ester, 6-amino-2- (4-bromophenyl) -5-chloro-4-pyr methyl imidin carboxylate, and 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidinecarboxylic acid. Also notable are the embodiments of herbicidal compositions of the present invention comprising the compounds of the embodiments described in the foregoing. This invention also relates to a method for removing unwanted vegetation, which comprises applying to the place of vegetation herbicidally effective amounts of the compounds of the invention (for example, as a composition described herein). They are to be noted as modalities in relation to the methods of use agüellas that involve the compounds of modalities described in the foregoing. Of note is a compound of formula I, which includes all geometric isomers and stereoisomers, N-oxides and agriculturally suitable salt thereof, agricultural compositions containing them and their use as herbicides, wherein R2 is C02R12, CH20R13, CHO, C (= N0R1) H, C (R15) (R16) C02R17 or C (= 0) N (R18) R19; each R7 is independently halogen, alkoyl of 1 to 4 carbon atoms, haloalguile of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 carbon atoms or haloalguiltium of 1 to 3 carbon atoms; R12 is H; or a radical which is selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alkylcycloalkyl of 4 to 12 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl of 2 to 14 carbon atoms carbon and alkynyl of 2 to 14 carbon atoms, each radical is optionally substituted with 1-3 of R27; R 13 is H, alkyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R28 or benzyl; R 14 is H, alkyl of 1 to 4 carbon atoms or haloalguile of 1 to 4 carbon atoms; R15 and R16 are independently H, halogen, alkoyl of 1 to 4 carbon atoms, haloalguile of 1 to 4 carbon atoms, hydroxy or alkoxy of 1 to 4 carbon atoms; R17 is alkenyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R29, or benzyl; R18 and R19 are independently H or alkenyl of 1 to 4 carbon atoms; each R27 is independently halogen, hydroxycarbonyl, alkoxycarbonyl of 2 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 carbon atoms, dialkylamino of 2 to 4 carbon atoms, -CH-f-0 (CH2) n ^ - or phenyl optionally substituted with 1-3 of R44; or two of R27 are taken together with the carbon atom to which they are attached to form a carbonyl moiety; each R and R is independently halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alguiltio of 1 to 4 carbon atoms, haloalguiltio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 carbon atoms or dialguilamino of 2 to 4 carbon atoms; each R, R31 and R32 is independently halogen, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, C 1 -C 4 alkylamino, dialkoxylamino of 2 to 4 carbon atoms or alkoxycarbonyl of 2 to 4 carbon atoms; each R38 is independently halogen, alkenyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkenylthio of 1 to 3 carbon atoms, haloalguiltium of 1 to 3 carbon atoms , amino, alkylamino of 1 to 3 carbon atoms, dialguilamino of 2 to 4 carbon atoms or alkoxycarbonyl of 2 to 4 carbon atoms; each R44 is independently halogen, alkoyl of 1 to 4 carbon atoms, haloalguilo of 1 to 3 carbon atoms-, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alguiltio of 1 to 3 carbon atoms, haloalguiltium of 1 to 3 carbon atoms, amino, alkylamino of 1 to 3 carbon atoms, dialguilamino of 2 to 4 carbon atoms or nitro; m is an integer from 2 to 5; and n is an integer from 1 to 4. In addition, it is noteworthy to note a compound of formula I, which includes all geometric isomers and stereoisomers, N-oxides or agriculturally suitable salts thereof, agricultural compositions containing them and their use as herbicides, wherein each R5 and R6 is independently halogen, alkoyl of 1 to 2 carbon atoms or haloalguilo of 1 to 2 carbon atoms; R15 is H, halogen, alkoyl of 1 to 4 carbon atoms, haloalguile of 1 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms or alkoylcarbonyloxy of 2 to 4 carbon atoms; R16 is H, halogen, alkenyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms; R24 is H, alkyl of 1 to 4 carbon atoms optionally substituted with 1-2 of R30, alkenyl of 2 to 4 carbon atoms optionally substituted with 1-2 of R31 or alkinyl of 2 to 4 carbon atoms optionally substituted with 1 -2 of R32; or R24 is C (= 0) R33, nitro, OR34, S (0) 2R35 or N (R36) R37; each R33 is independently H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms; alkoxy of 1 to 4 carbon atoms, phenoxy or benzyloxy; R34 is H, alkyl of 1 to 4 carbon atoms, haloalguile of 1 to 3 carbon atoms; and R36 is H or alkyl of 1 to 4 carbon atoms. The compounds of formula I can be prepared by one or more of the following methods and variations as described in reaction templates 1 to 7 and the accompanying text. The definitions of R, R1, R2, R3, R4, R5, R6, R7, R12 R13 R14 R15 R16 R17 R18 R19 R20 R21 R22 R23 R24 R25 r, r. , __, -, r, _ \, _ \, _ \, _ \, _ \, _ \, _ \, _ \, K, R27 R28 R29 R30 p31 R32 R33 R34 R35 R36 R37 R38 R39 R40 J? , _ \, _ \, -, r, _ \, K, -, _ \, K, -, i? , _ \, _ \, R41 R42 p 3 R44 R45 R46 R47 R48 R49 R50 R51 R53 R53 R54 r. , _-, r. , l \, - \, -, K, r_,? , _ \, r. , _ \, _ \, _ \, R55, R56, R57, R58, R59, R60, R61, Y, j, kyn in the compounds of the following formulas I to 12 are as defined above in the summary of the invention and in the description of the embodiments , unless otherwise indicated. The compounds of formula I can be prepared from chlorides of formula 2 by reaction with amines of formula 3, optionally in the presence of a base such as triethylamine or potassium carbonate, as indicated in reaction scheme 1. The reaction is It can be carried out in a variety of solvents including tetrahydrofuran, p-dioxane, ethanol and methanol with optimum temperatures ranging from room temperature to 200 ° C. The method of reaction scheme 1 is illustrated in step C of example 1, steps DI and D2 of example 2 and step B of example 4.
Reaction thread 1 The compounds of formula 2 can be prepared from hydroxy compounds of formula 4 (which can exist in the keto form) by reaction with a chlorinating reagent such as phosphorus oxychloride or thionyl chloride, optionally in the presence of such a base as N, N-dimethylaniline, as shown in the reaction enzyme 2. The reaction can be carried out neat or in the presence of a solvent such as N, N-dimethylformamide at temperatures ranging from room temperature to 120 ° C. . The method of the reaction enzyme 2 is illustrated in step C of example 1, steps Cl and C2 of example 2 and step B of example 4.
Reaction thread 2 The compounds of formula 4 can be prepared by the condensation of amidines of formula 5 with ketoesters of formula 6 in solvents such as methanol or ethanol at temperatures ranging from room temperature to the reflux temperature of the solvent, as shown in the chart Reaction 3. Optionally, a base such as a metal alkoxide or 1,1,3,3-tetramethylguanidine can be used. The method of reaction enzyme 3 is illustrated in step A of examples 1 and 4 and in steps Al and A2 of example 2.
Reaction thread 3 Wherein R80 is a carbon moiety such as algane, preferably alkenyl of 1 to 2 carbon atoms. The compounds of formula 4, wherein R 3 is a halogen can be prepared from compounds of formula 4 wherein R 3 is hydrogen, by reaction with a halogen such as bromine or a halogenating reagent such as an N-halosuccinimide or a sulfuryl in a variety of solvents which include acetic acid, N, N-dimethyl ormamide, dichloromethane, and carbon tetrachloride at temperatures ranging from 0-100 ° C, as shown in the reaction template 4. The reaction enzyme method 4 is illustrated in step B of example 1 and steps Bl and B2 of example 2.
Reaction scheme 4 halogenating reagent 4 ^ ^ * (R3 is H) (R3 is halogen) In addition, the compounds of formula I, wherein R 3 is a halogen can be prepared from compounds of formula I wherein R 3 is hydrogen by reaction with a halogenating reagent analogous to the method of the reaction scheme. This alternative method is illustrated in step C of example 4. A particularly useful preparation of the compounds of formula 4, wherein R3 is a halogen and R2 is C02R12 is the reaction of compounds of formula 4 wherein R3 is hydrogen and R2 is CH (OR12) 2 with a halogenating reagent and an oxidizing reagent such as N-halosuccinimide or bromine (when R3 is bromine) in a solvent such as dichloromethane, trichloromethane or tetrachloromethane at temperatures ranging from room temperature to the reflux temperature of the solvent, as shown in the reaction scheme 5. Reaction Scheme 5 Br2 (for R3 is Br) 02R12 ' The compounds of formulas 5 and 6 are commercially available or can be prepared by known methods (for example see: P. J. Dunn in Comprehensive Organic Functional Group Trans' format ions, A. R. Katritzky, O. Meth-Cohn; C. W. Rees Eds, Pergamon Press; Oxford, 1995; vol. 5, pp. 741-782; T. L. Gillchrist in Comprehensive Organic Functional Group Transformations, A. R. Katritzky, O. Meth-Cohn, C. W. Rees Eds., Pergamon Press; Oxford, 1995; vol. 6, pp. 601-637 and B. R. Davis, P. J. Garratt in Comprehensive Organic Synthesis, B. M. Trost Ed., Pergamon Press; Oxford, 1991; vol. 2, pp. 795-803). Alternatively, compounds of formula I can be prepared from the corresponding compounds of formula 7, wherein X 1 is a leaving group, such as a halogen or alkylsulfonyl group (for example methanesulfonyl, trifluoromethanesulfonyl, benzenesulfonyl), as shown in the reaction scheme 6. Reaction scheme 6 I (R is cyclopropyl, optionally substituted Pd isopropyl or phenyl ester) wherein M1 is B (OH) 2, Sn (n-Bu) 3, MgX1 or ZnX1; R1 is optionally substituted cyclopropyl, optionally substituted isopropyl or optionally substituted phenyl; and X1 is a leaving group. This method involves a palladium-catalyzed reaction of a compound of formula 7 with a compound of formula 8 in the form of a boronic acid (e.g., M1 is B (OH) 2), an organotin reagent (e.g., M1 is Sn (n-Bu) 3), a Grignard reagent (e.g. M1 is MgX1) or an organozinc reagent (e.g., M1 is ZnX1). (see for example: N. Ali, A. McKillop, M. Mitchell, R. Rebelo, A. Ricardo, P. Wallbank, tetrahedron, 1992, 48, 8117-8126; J. Solberg, K. Undheim, Acta Chem. Scand, 1989, 43, 62-68, V. Bonnet, F. mongin, F. Trécourt, G. Quéguiner and P. Knochel, Tetrahedron, 2002, 58, 4429-4438). The compounds of formula 7, wherein X 1 is a halogen can be prepared from dihalo compounds of formula 12 with an amine of formula 3 optionally catalyzed by a base such as triethylamine or potassium carbonate in a variety of solvents including tetrahydrofuran and dichloromethane at temperatures ranging from 0 ° C to the reflux temperature of the solvent, as shown in the reaction template 7.
Reaction run 7 7 (X is halogen) 12 (X is halogen) The compounds of formula 12 can be prepared by known methods (See, for example, H. Gershon, J. Org. Chem., 1962, 27, 3507-3510). As shown in reaction template 8, the compounds of formula I, wherein R2 is C02R12 can also be prepared from compounds of formula 13 by means of a carbonylation reaction Typical conditions are 1-10 atmospheres of monoxide carbon in the presence of a palladium catalyst in a mixture of an alcohol and another solvent such as N, N-dimethylformamide, N-methyl-pyrrolidinone or tetrahydrofuran at temperatures ranging from room temperature to 150 ° C.
Reaction scheme 8 13 (X is Cl or Br) As shown in Reaction Hose 9, compounds of Formula 13 can be prepared from compounds of Formula 14 by reaction with amines of Formula 3 in a reaction analogous to the reaction enzyme method 1.
Reaction Reactor 9 As shown in reaction template 10, compounds of formula 14 can be prepared from diols of formula 15 by reaction with a halogenating agent such as phosphorus oxychloride or phosphorus oxybromide in a reaction analogous to the reaction scheme method 2 (see H. Gershon, R. Braun, A. Scala and R. Rodin, J. Med. Chem 1964, 7, 808-811 and MH Norman, N. Chen, Z. Chen C. Fotsch, N. Han , R. Hurt, T. Jenkins J. Kincaid, L. Liu, Y. Lu, 0. Moreno, VJ Santora, JD Sonnenberg and W. Karbon, J. Med. Chem, 2000, 43, 4288-4312 for examples of this method, and for examples of preparation of compounds of formula 15).
Reaction scheme 10 fifteen The compounds of formula I, wherein R2 comprises an ester function (for example C02R12, wherein R12 is different from H), can be prepared from the corresponding carboxylic acid compounds of formula I (e.g., where R12 is H) by a wide variety of esterification methods known in the art. One method is illustrated in example 3. Conversely, the carboxylic acid compounds of formula I can be prepared from the corresponding ester compounds by a wide variety of hydrolysis methods known in the art, such as saponification. It is recognized that some reagents and reaction conditions described in the above for preparing compounds of formula I may not be compatible with certain functionalities present in the intermediates. In these cases, the incorporation of protection / deprotection sequences or interconversions of functional groups in the synthesis will help in the obtaining. of the desired products. The use and selection of protecting groups will be apparent to a person skilled in chemical synthesis (see, eg, T. W. Greene, P. G. Wuts, Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). A person skilled in the art will recognize that, in some cases, after the introduction of a given reagent as shown in many of the individual reaction templates, it may be necessary to perform additional systematic synthesis steps not described in detail for complete the synthesis of the compounds of formula I. A person skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above reaction schemes in an order different from that implied by the particular sequence presented to prepare the compounds of formula I. A person skilled in the art will also recognize that the compounds of formula I and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation and reduction reactions, and add substituents or modify existing substituents . Without further elaboration, it is considered that a person skilled in the art using the preceding description can use the present invention to its fullest extent. Therefore, the following examples should be considered only as illustrative and not limiting of the description in any way. The steps and the following examples illustrate a procedure for each step in a general synthesis transformation and the initial material of each step may not have been necessarily prepared by a particular preparative run whose procedure is described in other examples or steps. The percentages are by weight, except for mixtures of chromatographic solvent or when indicated in some other way. Parts and percentages for chromatographic solvent mixtures are by volume, unless otherwise indicated. The H-NMR spectra are reported in downfield ppm from tetramethylsilane, "s" means singlet, "d" means doublet, "t" means triplet, "c" means quartet, "m" means multiplet, " dd "means double of doublets," ddd "means doublet of doublet of doublets," dt "means doublet of triplets," of "means doublet of quartet," s broad "means broad singlet," broad "means broad doublet.
EXAMPLE 1 Preparation of ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate (Compound 1) and methyl 6-amino-5-bromo-2-cyclopropyl-4-pyridinecarboxylate (Compound 2) Step A: Preparation of 2-cyclopropyl-6- (diethoxymethyl) -4- (1H) -pyrimidinone To a mixture of ethyl 4,4-diethoxy-3-oxobutanoate (prepared according to the method of E. Graf, R. Troschutz, Synthesis, 1999, 7, 1216, 10.0 g, 46 mmol) and cyclopropanecarboximidamide monohydrochloride (Lancaster Synthesis, 5.0 g, 41 mmol) in 100 ml of methanol is added a methanol solution of sodium methoxide (5.4 M, 8.4 ml, 46 mmoles). The reaction mixture is stirred overnight. The solvent is separated with a rotary evaporator. Dichloromethane is added and the mixture is filtered. The filter solvent is separated with a rotary evaporator. The residue is purified by medium pressure flash chromatography (LCMS) (35-100% ethyl acetate in hexanes as eluent) to give the title compound as a white solid (4.67 g). XR NMR (CDC13) d 6.55 (s, 1H), 5.10 (s, 1H), 3.61 (m, 4H), 1.91 (, 1H), 1.23 (m, 8H), 1.09 (m, 2H). Additionally, 3.24 g of a non-dehydrated product are obtained. This material can be converted to the title compound by subjecting it to reflux in methanol with a catalytic amount of pyridinium p-toluenesulfonate. Step B: Preparation of ethyl 5-bromo-2-cyclopropyl-l, 6-dihydro-6-oxo-4-pyrimidinecarboxylate To a solution of 2-cyclopropyl-6- (diethoxymethyl) -4 (1H) -pyrimidinone (is say, the title product of step A) (2.9 g, 12.1 mmol) in 75 ml of dichloromethane is added N-bromosuccinimide (4.76 g, 26.8 mmol). The reaction mixture is stirred overnight. The solvent is separated with a rotary evaporator. The residue is purified by CLPM (1-> 4% methanol in dichloromethane as eluent) to provide the title compound as a white solid (2.68 g). XR NMR (CDC13) d 4.43 (c, 2H), 1.90 (m, 1H), 1.41 (t, 3H), 1.30 (m, 2H),. Step C: Preparation of ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate and methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate To a solution of 5-bromo-2- ethyl cyclopropyl-l, 6-dihydro-6-oxo-4-pyrimidinecarboxylate (i.e., the product of step B) (1.07 g, 3.7 mmol) in 15 ml of N, N-dimethylformamide is added thionyl chloride ( 0.54 ml, 7.5 mmol). The reaction mixture is stirred for 2 h. The solvent is separated with a rotary evaporator. The residue is dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate and dried with Na 2 SO 4. The solvent is separated with a rotary evaporator. The residue is dissolved in 2 ml of terahydrofuran and a methanolic solution of ammonia (7 N, 2 ml) is added. The reaction mixture is placed in a sealed flask and heated in a microwave reactor at 125 ° C for 2 h. The reaction mixture is allowed to stand over the weekend, dichloromethane is added and the reaction mixture is filtered. The solvent is separated with a rotary evaporator. The residue is purified by CLPM (10- »30% ethyl acetate in hexanes as eluent) to give the title product, a compound of the present invention, as a white solid (0.52 g). NMR Y. (CDC13) d 5.40 (broad s, 2H), 4.44 (c, 2H), 2. 05 (m, 1H), 1.01 (t, 3H), 1.05 (m, 2H), 0.99 (m, 2H). An isolated form of purification by HPLC is the corresponding methyl ester, ie, methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate, an additional compound of the present invention, as a white solid (0.06 g). Y NMR (CDCI3) d 5.40 (s, broad, 2H), 3.97 (s, 3H), 2.05 (m, 1H), 1.05 (m, 2H), 0.99 (m, 2H).
EXAMPLE 2 Preparation of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (Compound 135) Step Al: Preparation of 2-cyclopropyl-1, 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid To a mixture of diethyl oxaloacetate sodium salt (150 g, 714 mmol) in 300 ml of methanol and 150 ml of water is heated to 30 ° C and 50% aqueous sodium hydroxide (56 g, 700 mmol) in 60 ml of water is added during 30 minutes during which time the temperature it remains at 25-30 ° C and the pH at 11-12. Then, the stirred mixture is heated for an additional 30 min at 35 ° C. To this mixture is added cyclopropanecarboximidamide monohydrochloride (64 g, 530 moles) in portions, for 15 minutes. The orange solution is heated at 50 ° C for 30 minutes and kept at that temperature for 3 h. The reaction mixture is cooled to 35 ° C and concentrated hydrochloric acid (approximately 70 g, 0.7 mol) is gradually added (resulting in foaming) for 30 minutes at 30-40 ° C until the pH is about 1.5. -2.5. The mixture is concentrated with a rotary evaporator at 35-40 ° C to separate the alcohols, stirred for 3-4 h at 25 ° C for complete crystallization of the product. After the mixture is cooled to 0 ° C, the solid is collected by filtration. The solid is washed with water (2 x 60 ml), dried by suction and then dried in a vacuum oven at 60 ° C to provide the title compound as a beige solid (approximately 60 g). NMR Y (DMS0-d6) d 6.58 (s, 1H), 1.95 (, 1H), 1.0 (m, 4H). Step A2: Another preparation of 2-cyclopropyl-1, 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid To a mixture of the sodium salt of diethyl oxaloacetate (210 g, 950 mmol) in 500 ml of methanol and 400 ml of water is added 50% aqueous sodium hydroxide (80 g, 1.0 mole) in 60 ml of water for 30 minutes, during which time the temperature remains at 25-30 ° C and the pH at 11-12.
Then the stirred mixture is heated for an additional 30 min at 30 ° C. To this mixture is added cyclopropanecarboximidamide monohydrochloride (110 g, 910 moles). The orange solution is heated at 50 ° C for 30 minutes and kept at that temperature for 5 h. The reaction mixture is cooled to 30 ° C and concentrated to half its volume under reduced pressure, at 35-40 ° C and concentrated hydrochloric acid (140 g, 1.4 moles) is gradually added (resulting in foaming) for 30 minutes at 25-30 ° C until the pH is about 1-2. The mixture is stirred at 5 ° C for 1 h to complete the crystallization of the product. The mixture is then cooled to 0 ° C and the solid is collected by filtration. The solid is washed with water (3 x 60 ml), dried by suction and then dried in a vacuum oven at 70 ° C to provide the title compound as a beige solid (100 g); p. F. 235-236 ° C (decomposition). NMR Y (DMSO-d6) d 6.58 (s, 1H), 1.95 (m, 1H), 1.0 (m, 4H). Step Bl: Preparation of 5-chloro-2-cyclopropyl-l, 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid To a mixture of 2-cyclopropyl-l, 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid ( that is, the product of stage Al or A2) (9.2 g, 52 mmol) in 30 ml of water and concentrated hydrochloric acid (22 g, 220 mmol) at 15 ° C is added dropwise to an aqueous solution of sodium hypochlorite (11%, 40 g, 59 mmol) for 15 minutes so that, with cooling, the reaction mixture is maintained at 15-20 ° C. The mixture is then kept at 20-25 ° C for 1 h. About 2 g of solid sodium bisulfite are added and then the aqueous solution of sodium hydroxide (50%, 8 g, 0.10 mol) is added dropwise so that with cooling the reaction mixture is maintained at about 25 ° C. . The mixture is cooled to 10 ° C and the suspended product is isolated by filtration and washed with a minimum amount of cold water. The product is then dried to constant weight in a vacuum oven at 50 ° C to provide the title compound (7.5 g). NMR Y (DMSO-d6) d 13.4 (broad s, 1H), 1.95 (m, 1H), 1.0 (m, 4H). Step B2: Another preparation of 5-chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid To a mixture of 2-cyclopropyl-l, 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (ie, the product of stage Al or A2) (184 g, 1.02 mol) in 45 ml of water and concentrated hydrochloric acid (292 g, 3 mol) at 8-12 ° C is added dropwise an aqueous solution of sodium hypochlorite (8.4%, 1.02 kg, 1.15 moles) for 2 h, so that with cooling the reaction mixture is maintained at 8-10 ° C. The mixture is then maintained at 10-12 ° C for 1 h and the conversion is monitored by CLAR. When less than 5% of the initial material remains, solid sodium bisulfite is added until a paper test of negative Kl starch is obtained. The mixture is cooled to 5 ° C and the suspended product is isolated by filtration and washed with a minimum amount of cold water. The product is then dried to constant weight in a vacuum oven at 50 ° C to provide the title compound (194 g), p. F. 189-190 ° C. NMR aH (DMSO-d6) d 13.4 (broad s, 1H), 1.95 (m, 1H), 1.0 (m, 4H). Step Cl: Preparation of 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid Combine phosphorus oxychloride (14 ml, 23 g, 0.15 mol) and 5-chloro-2-cyclopropyl-l, 6-dihydroxy acid. 6-oxo-4-pyrimidinecarboxylic acid (ie, product 1 from step Bl or B2) (75 g, 300 mmol) and heated at 85 ° C for 3 h. The reaction mixture is cooled to 30 ° C and added for 30 minutes to a mixture of 50 ml of acetonitrile and 80 ml of ice water, and the temperature is maintained at 5-10 ° C and the pH is maintained at room temperature. 1-3 interval by co-feeding aqueous ammonia (28%). The pH is adjusted to about 2, the mixture is concentrated at 25 ° C with a rotary evaporator to remove acetonitrile and the precipitated product is isolated by filtration and washed with water (2 x 25 ml). The solid is dried in a vacuum oven to provide the title compound (approximately 7.0 g).
NMR Y. (DMSO-de) d 2.23 (m, 1H), 1.2 (m, 2H), 1.0 (m, 2H). Step C2: Another preparation of 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid Combine phosphorus oxychloride (200 ml, 328 g, 2. 14 moles) and 5-chloro-2-cyclopropyl-l, 6-dihydro-6-oxo-4-pyrimidinecarboxylic acid (i.e., the product of step Bl or B2) (96.8 g, 451 mmol) and heated to 90 ° C for 5 h. The reaction mixture is cooled to 50-60 ° C and concentrated under reduced pressure to half the volume. After cooling to 30 ° C, the reaction mixture is added over 60 minutes to a mixture of 200 ml of terbutanol and 300 ml of water, and the temperature is maintained at 8-10 ° C. The mixture is seeded, 300 ml of water are gradually added at 10-15 ° C and the mixture is stirred for 1 h. After cooling to 5 ° C the precipitated product is isolated by filtration and washed with water (3 x 50 ml). The solid is dried in a vacuum oven to provide the title compound (930 g). NMR Y (DMSO-d6) d 2.23 (m, 1H), 1.2 (m, 2H), 1.0 (m, 2H). Step DI: Preparation of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid A mixture of 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (ie, the product in stage Cl or C2) ) (5.1 g, 22 mmol), 30 ml of water and aqueous ammonia (28%, 8 g, 130 mmol) is heated at 80 ° C for 3 h. The solution is concentrated at 50 ° C and a pressure of 70 torr (9.3 kPa) to approximately half the volume to remove most of the excess ammonia. The resulting suspension is stirred at 20 ° C, acidified to pH 2 with aqueous hydrochloric acid, cooled to 5 ° C and filtered. The isolated solid is dried in a vacuum oven to provide the title product (4.2 g), a compound of the present invention. NMR Y (DMSO-d6) d 13.4 (broad s, 1H), 1.95 (m, 1H), 1.0 (m, 4H). Step D2: Another preparation of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid A mixture of 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (ie the product of step Cl or C2) ) (280 g, 1.2 moles), 1.26 1 of water and aqueous ammonia (28%, 350 g, 5.76 moles) is heated at 80 ° C for 5 h. The solution is concentrated at 50 ° C and a pressure of 70 torr (9.3 kPa) to approximately half the volume to remove most of the excess ammonia. The resulting suspension is stirred at 20 ° C, acidified to pH 1-2 with aqueous hydrochloric acid, cooled to 5 ° C and filtered. The isolated solid is dried in a vacuum oven to provide the title product (270 g), a compound of the present invention. RMN ^? (DMSO-d6) d 13.4 (broad s, 1H), 1.95 (m, 1H), 1.0 (m, 4H).
EXAMPLE 3 Preparation of methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate (Compound 9) To a solution of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product from step DI or D2 of example 2) (2.0 g, 8.5 mmol) in 20 ml of methanol is added dropwise thionyl chloride (4 ml, 70 mmol). The mixture is refluxed for 24 h. 5 drops of concentrated sulfuric acid are added and the reaction mixture is heated to reflux for 16 h. After the mixture is cooled, 30 ml of water are added and aqueous ammonia (28%, 10 ml) is added dropwise. The mixture is cooled to 5 ° C and the solid isolated by filtration, washed with water and dried in a vacuum oven at 40 ° C to provide the title product (2.3 g), a compound of the present invention. NMR Y (CDC13) d 5.4 (broad s, 2H), 3.98 (s, 3H), 2.06 (, 1H), 1.04 (m, 2H), 1.00 (m, 2H). Another preparation of methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate To a solution of 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (i.e. the product of step DI or D2 from example 2) (8.5 g, 40 mmol) in 120 ml of methanol is added dropwise with cooling thionyl chloride (15 ml, 200 mmol). The mixture is heated at 60 ° C for 24 h. The mixture is concentrated to 25% of the original volume and diluted with 100 ml of water. PH indicator, phenolphthalein is added, and 10% aqueous sodium hydroxide drops are added, with cooling at 10-20 ° C until reaching a pH of 8-10. The solid is isolated by filtration, washed with water and dried in a vacuum oven at 50-60 ° C to provide the title product (7.3 g), a compound of the present invention. NMR Y (CDC13) d 5.41 (broad s, 2H), 3.98 (s, 3H), 2.06 (, 1H), 1.04 (m, 2H), 1.00 (, 2H).
Example 4 Preparation of 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidinecarboxylic acid (Compound 65) Step A: Preparation of 2- (4-chlorophenyl) -1,6-dihydro-6- oxo-4-pyrimidinecarboxylic acid To a mixture of the diethyl oxaloacetate sodium salt (123.2 g, 586 mmoles) in 750 ml of water are slowly added aqueous sodium hydroxide (50%, 47 g, 586 mmoles). After 1 h, the solids have dissolved. Then 4-chlorobenzenecarboximidamide monohydrochloride (111.95 g, 586 mmol) is added and the mixture is heated at 70 ° C overnight. After cooling to room temperature, concentrated hydrochloric acid (which provokes foaming) is slowly added until the pH drops to 1.5. The solid is isolated by filtration and washed with water and methanol. The solid is then triturated twice with hot methanol, washed repeatedly with 1 N hydrochloric acid and then once with methanol and dried to give the title compound (66.07 g). NMR Y (DMSO-de) d 8.23 (d, 2H), 7.65 (d, 2H), 3.90 (s, 1H). Step B: Preparation of 6-amino-2- (4-chlorophenyl) -4-pyrimidinecarboxylic acid To 180 ml of phosphorus oxychloride add 2- (4-chlorophenyl) -1,6-dihydro-6-oxo-4 -pyrimidinecarboxylic acid (ie, the product of stage A) (81.81 g, 326 immoles). The mixture is heated at 90 ° C for 2.5 h. After cooling to room temperature, the reaction mixture is added slowly to 1: 2 acetonitrile: water 1.5 1 while maintaining the temperature between 35 and 45 ° C. After the reaction mixture is stirred at room temperature for 30 minutes the resulting solid is isolated by filtration and washed with water. The solid is then combined with aqueous ammonia (5%, 2.1 1) and heated at 80 ° C for 18 h. After 2 days at room temperature, the solid is isolated by filtration and washed with water. A second crop is obtained by cooling the filtrate and refiltering. The combined solids are dried to provide the title compound (58.8 g). 1 H NMR (DMSO-de) d 8.33 (d, 2H), 7.51 (d, 2H), 6.89 (s, 2H), 6.81 (s, 1H). Step C: Preparation of 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidinecarboxylic acid To a solution of 6-amino-2- (4-chlorophenyl) -4-pyrimidinecarboxylic acid (i.e. product of stage B) (75 g, 300 mmol) in 300 ml of N, N-dimethylformamide at 50 ° C is added in portions N-chlorosuccinimide (44.1 g, 330 mmol). The temperature of the reaction mixture increases exothermically at 65 ° C. Then the reaction mixture is heated at 55 ° C for 3 h. Additional N-chlorosuccinimide (14 g, 90 mmol) is added in portions and the reaction mixture is maintained at 55 ° C for 30 minutes.
After the reaction mixture is cooled, water is added. The resulting solid is isolated by filtration, washed with water, dissolved in ethyl acetate, washed with water and dried. The solvent is removed using a rotary evaporator to provide the title product, a compound of the present invention, as a tan solid. (73.68 g). NMR I (DMSO-de) d 8.28 (d, 2H), 7.70 (broad s, 2H), 7.58 (d, 2H).
EXAMPLE 5 Preparation of ethyl 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidinecarboxylate (Compound 64) To a solution of 6-amino-5-chloro-2- (4-chlorophenyl) - 4-pyrimidinecarboxylic acid (ie, the product of Example 4, step C) (20.0 g, 70.4 mmol) in 70 ml of ethanol is added thionyl chloride (5.14 ml, 70.4 mmol) while maintaining the temperature below 15 °. C using an ice bath. The reaction mixture is then heated to reflux overnight. Water is added. After with external cooling, aqueous sodium hydroxide (50%) is added to adjust the pH to 7. The resulting solid is isolated by filtration and dried to provide the title product, a compound of the present invention, as a beige solid clear (20.1 g). NMR Y. (CDC13) d 8.31 (d, 2H), 7.42 (d, 2H), 5.50 (broad s, 2H), 4.50 (c, 2H), 1.47 (t, 3H). The following compounds of Tables 1 to 4 can be prepared by the methods described herein in conjunction with the methods known in the art. The following abbreviations are used in the following tables: t means tertiary, i means iso, Me means methyl , Et means ethyl, Pr means propyl, i-Pr means isopropyl, Bu means butyl, t-Bu means terbutyl, CN means cyano and S (0) 2 Me means methanesulfonyl. The symbol "?" means a negative formal charge and the "®" sign means a positive formal charge.
TABLE 1 C02CH2Ph C02CH2Ph C02CH2Ph C02CH2Ph C02CH (Me) Ph C02CH (Me) Ph C02CH (Me) Ph C02CH (Me) Ph C02CH2 (4-Cl-Ph) C02CH2 (4-Cl-Ph) C02CH2 (4-Cl-Ph) C02CH2 (4-Cl-Ph) C02CH2 (3-F-Ph) C02CH2 (3-F-Ph) C02CH2 (3-F-Ph) C02CH2 (3-F-Ph) C02CH2CH2NMe2 C02CH2CH2NMe2 C02CH2CH2NMe2 C02CH2CH2NMe2 C02CH2CH2OMe C02CH2CH2OMe C02CH2CH2OMe C02CH2CH2OMe C02CH2CH2OH C02CH2CH2OH C02CH2CH2OH C02CH2CH2OH C02CH2 (3- C02CH2 (3- C02CH2 (3- C02CH2 (3-oxetanyl) oxetanyl) oxetanyl) oxetanyl) CH2OH CH2OH CH2OH CH2OH CH2OMe CH2OMe CH2OMe CH2OMe CH2C02Me CH2C02Me CH2C02Me CH2C02Me CH (OH) C02Me CH (OH) C02Me CH (OH) C02Me CH (OH) C02Me CH (OC (= 0) Me) - CH (OC (= 0) Me) - CH (OC (= 0) Me) - CH (OC (= 0) Me) - C02Me C02Me C02Me C02Me CHO CHO CHO CHO C ( = NOH) HC (= NOH) HC (= NOH) HC (= NOH) HC (= NOMe) HC (= NOMe) HC (= NOMe) HC (= NOMe) HC (= 0) NH2 C (= 0) NH2 C (= 0) NH2 C (= 0) NH2 C (= 0) NHMe C (= 0) NHMe C (= 0) NHMe C (= 0) NHMe C (= 0) NHMe2 C (= 0) NHMe2 C (= 0) = 0) NHMe2 C (= 0) NHMe2 C02Ph C02Ph C02Ph C02Ph C (0) O? H3N®Me C (0) O? H3N®Me C (0) O? H3N®Me C (0) O? H3N®Me C (0) O? H3N®i-Pr C (0) O? H3N®I-Pr C (0) O? H3N®i-Pr C (0) O? H3N®i-Pr C (0) O? H3N®Pr C (0) O? H3N®Pr C (0) O? H3N®Pr C (0) O? H3N®Pr C (0) O? H3N®butyl C (0) O? H3N®butyl C (0) O? H3N®butyl C (0) O? H3N®butyl C (0) O? H3N®hexyl C (0) O? H3N®hexyl C (0) O? H3N®hexyl C (0) O? H3NHhexyl C (0) 0 ° H3Nighty C (0) 0 ° H3Nightyl C (0) 0 ° H3Nightylctyl .C (0) 0BH3N? Octyl C (0) 0 ° H3Nw ~ C (0) 0TH3N® ~ C (0) 0 ° H3Nw C (0) 0? H3N® ~ hexadecyl hexadecyl hexadecyl hexadecyl C (0) O? H3N® ~ C (0) 0? H3N® ~ C (0) 0TH3NF_ C (0) 0? H3N® ~ octadecyl octadecyl octadecyl octadecyl C (0) 0TH3N®- C (0) 0? H3N? "C (0) 0? H3N® ~ C (0) 0? H3N® ~ cyclohexyl cyclohexyl cyclohexyl cyclohexyl C (0) 0? H2N® (Et) 2 C (0) O? H2N® (Et) 2 C (0) O? H2N® (Et) 2 C (0) O? H2N® (Et) 2 C (0) 0T C (0) O? C (0) 0T C (0) O? H2N® + (CH2) 20- H2N®- (CH2) 20- H2N®-f (CH2) 20- H2NT- (CH2) 20- (CH2) 2 + - (CH2) 2 + - (CH2) 2 + - (CH2) 21 C (0) 0T C (0) O? C (0) 0T C (0) 0? H2N®-fCH2- H2N®- CH2- H2N®- CH2- H2N®-fCH2- (CH2) 2CH2 + - (CH2) 2CH2 + (CH2) 2CH2 + - (CH2) 2CH2X- C (0) 0? NH® (Et) 3 C (0) O? NH? (Et) 3 C (0) O? NH? (Et) 3 C (0) O? NH? (Et) 3 C (0) O? N? (Me) C (O)? 0) O? N (R) (Me) 4 C (O) O? N? (Me) 4 C (O) O? N (Me) 4 C (0) O? N (R) (Me) 3- C (O) O? N (R) (Me) 3- C (O) N? N (Me) 3- C (O) N? N (Me) 3-CH2Ph • CH2Ph CH2Ph CH2Ph C (0) O? S® (Me) 3 C (0) OeS® (Me) 3 C (0) O? S® (Me) 3 C (0) O? S® ( Me) 3 C (0) 0TK® C (0) 0? K® C (0) O? K® C (0) 0TK® 4-Cl-Ph; I.
C02Me C02Me C02Me C02Me C02Et C02Et C02Et C02Et C02Pr C02Pr C02Pr C02Pr C02iPr C02iPr C02iPr C02iPr C02tBu C02tBu C02tBu C02tBu C02ciclohexilo C02ciclohexilo C02cíclohexilo C02ciclohexilo C 2 -hexyl C02hexyl C02hexyl C02hexyl C02CH2_ C02CH2- C02CH2_ C02CH2_ cyclohexyl cyclohexyl cyclohexyl cyclohexyl C02CH2Ph C02CH2Ph C02CH2Ph C02CH2Ph C02CH (Me) Ph C02CH (Me) Ph C02CH (Me) Ph C02CH (Me) Ph C02CH2 (4-Cl-Ph) C02CH2 (4-Cl-Ph) C02CH2 (4-Cl-Ph) C02CH2 (4-Cl-Ph) C02CH2 (3-F-Ph) C02CH2 (3-F-Ph) C02CH2 (3-F-Ph) C02CH2 (3-F-Ph) C02CH2CH2NMe2 C02CH2CH2NMe2 C02CH2CH2NMe2 C02CH2CH2NMe2 C02CH2CH2OMe C02CH2CH20Me C02CH2CH2OMe C02CH2CH2OMe C02CH2CH2OH C02CH2CH2OH C02CH2CH2OH C02CH2CH2OH C02CH2 (3- C02CH2 (3- C02CH2 (3- C02CH2 (3-oxetanyl) oxetanyl) oxetanyl) oxetanyl) CH 2 CH 2 OH CH 2 OH CH 2 OH CH 2 OM CH 2 OM CH 2 O CH Me CH 2 CO 2 Me CH 2 CO 2 Me CH 2 O 2 Me CH 2 O 2 Me CH 2 O 2 Me CH 2 O 2 Me CH 2 O 2 O CH (OH) C O 2 Me CHO CHO CHO CHO CH (OC (= 0) Me) - CH (OC (= 0) Me) - CH (OC (= 0) Me) - CH (0C (= 0) Me) - C02Me C02Me C02Me C02Me C (= NOH) HC (= N0H) HC (= NOH) HC (= NOH) HC (= NOMe) HC (= NOMe) HC (= NOMe) HC (= NOMe) H C (= 0) NH2 C (= 0) NH2 C (= 0) NH2 C (= 0) NH2 C (= 0) NHMe C (= 0) NHMe C (= 0) NHMe C (= 0) NHMe C (= 0) NHMe2 C (= 0) NHMe2 C (= 0) NHMe2 C (= 0) NHMe2 C (0) 0SH3NW "C (0) 0 ° H3Nw ~ C (0) 0HH3Nw" C (0) 0tíH3Nw ~ octadecyl octadecyl octadecyl octadecyl C (0) 0? H3N® ~ C (0) 0? H3N® ~ C (0) 0TH3N® "C (0) 0? H3N® ~ cyclohexyl cyclohexyl cyclohexyl cyclohexyl C (0) 0? H2N® (Et) 2 C (0) 0? H2N® (Et) 2 C (0) O? H2N® (Et) 2 C (0) 0? H2N® (Et) 2 C (0) 0T C (0) 0T C (0) O? C (0) 0T H2N®- £ - (CH2) 20- H2N®-f (CH2) 20- H2N® + - (CH2) 20- H2N®- (CH2) 20- (CH2) 2+ (CH2) 2 (CH2) 2+ (CH2) 2 + -C (0) 0T C (0) 0T C (0) 0T C (0) O? H2N®- CH2- H2N®- CH2- H2N®- CH2- H2N®- CH2- (CH2) 2CH2 + - (CH2) 2CH2 - (CH2) 2CH2 ^ (CH2) 2CH2 ^ C (0) 0? NH® (Et) 3 C (0) 0? NH® (Et) 3 C (0) O? NH® (Et) 3 C (0) O? NH® (Et) 3 C ( 0) 0? N (Me) 4 C (0) 0? NF (Me) 4 C (0) O? N (Me) 4 C (0) O? N (Me) 4 C (0) O? N (R) (Me) 3- C (O) O? N (R) (Me) 3- C (O) N? N (Me) 3- C (O) N? N (Me) 3-CH2Ph CH2Ph CH2Ph CH2Ph C (0) O? S® (Me) 3 C (0) O? S® (Me) 3 C (0) O? S® (Me) 3 C (0) O? S® (Me) 3 C (0) 0TK® C (0) 0TK® C (0) 0TK® C (0) 0TK® TABLE 2 R 'R ~ ~ N '• H R2 is C02H; R3 is Cl R2 is C02Me; R3 is R2 is C02Et; R3 is Cl Cl R? Et i-Pr i-Pr i-Pr 1-Me-cyclopropyl 1-Me-cyclopropyl 1-Me-cyclopropyl 2-Me-cyclopropyl 2-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-F-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2-Cl-cyclopropyl 2-Cl-cyclopropyl 2,2-Di-F- 2,2-di-F- 2,2-di-F-cyclopropyl cyclopropyl cyclopropyl 2,2-di-Cl- 2,2-di-Cl- 2,2-di-Cl cyclopropyl cyclopropyl cyclopropyl 1,2-di-F-1,2-di-F-1,2-di-F-cyclopropyl cyclopropyl cyclopropyl 2,2,3, 3-tetra-F- 2,2,3, 3 -tetra-F- 2,2,3,3-tetra-F-cyclopropyl cyclopropyl cyclopropyl 1,2,2,3,3-penta-F-1,2,2,3,3-penta-F-1, 2,2,3,3-penta-F-cyclopropyl cyclopropyl cyclopropyl Ph Ph Ph 4-Cl-Ph 4 -Cl-Ph 4 -Cl-Ph 4-F-Ph 4-F-Ph 4 -F-Ph 3 - OMe-Ph 3 -OMe-Ph 3 -OMe-Ph 4-Br-Ph 4-Br-Ph 4-Br-Ph 4 -I-Ph 4-I-Ph 4 -I-Ph 4-CF3-Ph 4- CF3-Ph 4 -CF3-Ph 4-0CHF2-Ph 4 -OCHF2-Ph 4 -OCHF2-Ph 4 -OCF3-Ph 4 -0CF3-Ph 4 -OCF3-Ph 4-SCF3-Ph 4-SCF3-Ph 4 - SCF3-Ph 4-SCHF2-Ph 4-SCHF2-Ph 4 -SCHF2-Ph 4-CN-Ph 4-CN-Ph 4-CN-Ph 4-C02Me-Ph -C02Me -Ph 4-C02Me-Ph 2.4 -di-Cl-Ph 2,4-di-Cl-Ph 2,4-di-Cl-Ph 2-F-4-Cl-Ph 2-F-4-Cl-Ph 2-F-4-Cl- Ph 3,4-di-Cl-Ph 3,4-di-Cl-Ph 3,4-di-Cl-Ph 2 -MeO-2-MeO-cyclopropyl 2-Me-cyclopropyl cyclopropyl 2-MeS-2-MeS -cyclopropyl 2-MeS-cyclopropyl cyclopropyl CH (Me) CH2OMe CH (Me) CH, OMe CH (Me) CH2OMe R2 is C02H; R3 is Br R2 is C02Me; R3 is R2 is C02Et; R3 is Br Br R1 Ei Ei i-Pr i-Pr i-Pr 1-Me-cyclopropyl 1-Me-cyclopropyl 1-Me-cyclopropyl 2-Me-cyclopropyl 2-Me-cyclopropyl 2-Me-cyclopropyl 2-F-cyclopropyl 2-F-cyclopropyl 2-F-cyclopropyl 2-Cl-cyclopropyl 2-Cl-cyclopropyl 2-Cl-cyclopropyl 2, 2-di-F-cyclopropyl 2,2-di-F- 2,2-di-F-cyclopropyl cyclopropyl 2,2-di-Cl- 2,2-di-Cl- 2,2-di-Cl-cyclopropyl cyclopropyl cyclopropyl 1,2-di-F-cyclopropyl 1,2-di-F- 1,2-di- F-cyclopropyl 2,2,3,3-tetra-F-2,2,3,3-tetra-F-2,2,3,3-tetra-F-cyclopropyl cyclopropyl cyclopropyl 1,2,2,3 , 3-penta-F- 1,2,2,3, 3-penta-F- 1,2,2,3,3-penta-F-cyclopropyl cyclopropyl cyclopropyl Ph Ph Ph 4-Cl-Ph 4-Cl- Ph 4-Cl-Ph 4-F-Ph 4-F-Ph 4-F-Ph 3-OMe-Ph 3-OMe-Ph 3-OMe-Ph 4-Br-Ph 4-Br-Ph 4-Br-Ph Ph 4-I-Ph 4-I-Ph 4-I-Ph 4-CF3-Ph 4-CF3-Ph 4-CF3-Ph 4-OCHF, -Ph 4-OCHF2-Ph 4-OCHF2-Ph 4-OCF3 -Ph 4-OCF3-Ph 4-OCF3-Ph 4-SCF3-Ph 4-SCF3-Ph 4-SCF3-Ph 4-SCHF2-Ph 4-SCHF2-Ph 4-SCHF2-Ph 4-CN-Ph 4-CN -Ph 4-CN-Ph 4-C02Me-Ph 4-C02Me-Ph 4-C02Me-Ph 2,4-di-Cl-Ph 2,4-di-Cl-Ph 2,4-di-Cl-Ph 2 -F-4-Cl-Ph 2-F-4-Cl-Ph 2-F-4-Cl-Ph 3,4-di-Cl-Ph 3,4-di-Cl-Ph 3,4-di- Cl-Ph 2-MeO-cyclopropyl 2-MeO-cyclopropyl 2-MeO-cyclopropyl 2-MeS-cyclopropyl 2-MeS-cyclopropyl 2-MeS-cyclopropyl CH (Me) CH2OMe CH (Me) CH2OMe CH (Me) CH2OMe TABLE 3 cyclopropyl; R2 is TABLE 4 NHS (O) 2Me NHS (0) 2Me NHS (0) 2Me NHS (0) 2Me NHNH2 NHNH2 NHNH. NHNH2 NHN02 NHN02 NHNO, NHNO. N = CHNMe2 N = CHNMe2 NHOH NHOH NHOMe NHOMe NHCH2C02Me NHCH2C02Me NHCH2C02Et NHCH2C02Et NHCH2CH2OH NHCH2CH2OH NHCH2CH2OMe NHCH2CH2OMe NHCH2CH2NMe2 NHCH2CH2NMe2 NHCH, CH, NMe, NHCH2CH2NMe2 NHCH2C02Me NHCH2C02Me NHCH2C02Me NHCH2C02Me NHCH2C02Et NHCH2C02Et NHCH2C02Et? HCH2C02Et NHCH2CH2OH NHCH2CH2OH NHCH2CH2OH? HCH2CH2OH NHCH2CH2OMe NHCH2CH2OMe NHCH2CH2OMe? HCH2CH2OMe NHCH2CH2NMe2 NHCH. CH.NMe, NHCH2CH2NMe2? HCH2CH2? Me2 Formulation / Utility The compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a diluent, a solid diluent or a surfactant. The formulation or ingredients of the composition are selected to match the physical properties of the active ingredient, the mode of application and environmental factors such as soil type, humidity and temperature. Useful formulations include such liquids as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and / or suspoemulsions) and the like which optionally can be thickened in gels. Useful formulations further include solids such as fine powders, powders, granules, pellets, tablets, films (including seed coatings) and the like which may be water dispersible ("wettable") or water soluble. The active ingredient can be (micro) encapsulated and can be further formed into a suspension or solid formulation; alternatively the entire formulation of the active ingredient may be encapsulated (or "overcoated"). The encapsulation can control or delay the release of the active ingredient. The formulations susceptible to be sprayed can be diluted in suitable media and can be used in spray volumes from approximately one to several hundred liters per hectare. High strength compositions are used primarily as intermediates for subsequent formulations. The formulation will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which are summed to be weight percent.
Percent by weight Ingredient Thinner Active surfactant Granules, tablets and powders 0.001-90 0-99.999 0-15 dispersible in water and water soluble Suspensions, emulsions, 1-50 40-99 0-50 solutions (including emulsifiable concentrates Fine powders 1- 25 70-99 0 - 5 Granules and Pellets 0,001-99 5-99,999 0-15 High Compositions 90 -99 0 -10 0 -2 Resistance Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, include lists of surfactants and recommended uses. formulations may contain minor amounts of additives to reduce r foaming, tasting, corrosion, microbiological growth and the like or thickeners to increase viscosity. Surfactants include, for example, polyethoxylated alcohols, polyethoxylated algilphenols, polyethoxylated sorbitan fatty acid esters, dialguyl sulfosuccinates, algayl sulfates, albuylbenzene sulfonates, organosilicones, N, N-dialkyl taurates, lignin sulfonates, sulfonate condensates. of naphthalene and formaldehyde, polycarboxylates, glycerol esters, polyoxyethylene / polyoxypropylene blog copolymers and aligyl polyglucosides wherein the number of glucose units, termed as the degree of polymerization (DP) can vary from 1 to 3 and alkyl units they can vary from 6 to 14 carbon atoms (see Pure and Applied Chemistry 72, 1255-1264). Solid diluents include, for example, clay such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, carbonate and sodium bicarbonate and sodium sulfate. The liquefied diluents include, for example, water, N, N-dimethylformamide, dimethyl sulfoxide, N-allylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, glycerin, triacetin, olive oils, oil of castor, linseed, aleurite, sesame, corn, peanut, cottonseed, soybean, colsa and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2- pentanone, acetates such as hexyl acetate, heptyl acetate and octyl acetate and alcohols such as methanol, cyclohexanol, decanol, benzyl alcohol and tetrahydrofuryl. Useful formulations of this invention may also contain materials well known to those skilled in the art as formulation aids such as defoamers, film formers and dyes. Defoamers may include water dispersible liquids comprising polyorganosiloxanes such as Rhodorsil ™ 416. Film formers may include polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. The dyes may include liquid water dispersible compositions such as the red dye Pro-Ized ™. A person skilled in the art will appreciate that this is not an exhaustive list of formulation aids. Suitable examples of formulation aids include those which are included in the present listing and which are mentioned in McCutcheon '' s 2001, Volume 2: Functional Materials published by MC Publishing Company and PCT publication WO 03/024222. The solutions, which include emulsifiable concentrates, can be prepared by simply mixing the ingredients. Fine powders and powders can be prepared by combination and, usually, ground as in a hammer mill or a fluid energy mill. The suspensions are usually prepared by wet grinding; see, for example, the document of U.A. 3,060,084. Granules and pellets can be prepared by spraying active material on preformed granular carriers or by agglomeration techniques. See, Browning, "Agglomeration," Chemical Engineering, December 4, 1967, pp. 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 et seq. and WO 91/13546. The pellets can be prepared as described in the document of US Pat. No. 4,172,714. The water-dispersible and water-soluble granules can be prepared as described in the documents of US Pat. No. 4,144,050, 3,920,442 and DE 3,246,493. The tablets can be prepared as described in the documents of US Pat. No. 5,180,587, 5,232,701 and 5,208,030. The films can be prepared as described in GB 2,095,558 and E. U: A 3,299,566. For additional information regarding the formulation art see TS Woods, "The Formulator's Toolbox-Product Forms for Modern Agriculture" in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and TR Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, p. 120-133. See also the document of U.A.A. 3,235,361, Col. 6, line 16 to Col. 7, line 19 and examples 10-41; US 3,309,192, Col. 5, line 43 to Col. 7, line 62 and examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; document of E. U. A. 2,891,855, Col. 3, line 66 to Col. 5, line 17 and examples 1-4; Klingman, Weed Controls as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in Formulation Technology, PJB Publications, Richmond, UK, 2000. In the following examples, all percentages are by weight and all formulations are prepared in a conventional manner. Compound numbers refer to compounds in the index A-D tables.
Example A High strength concentrate Compound 1 98.5% silica airgel 0.5% synthetic amorphous fine silica 1.0% Example B Wettable powder Compound 2 65.0% dodecylphenol polietielnglycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0% Example C Granule Compound 4 10.0% attapulgite granule (low volatility material, o.71 / 0.30 mm; US sieves No. 25-50) 90.0% Example D Aqueous suspension Compound 9 25.0% hydrated attapulgite - 3.0% crude calcium ligninsulfonate 10.0% sodium diacid phosphate 0.5% water 61.5% Example E Extruded pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% raw calcium ligninsulfonate 5.0% sodium alguilnaphthalenesulfonate 1.5% calcium / magnesium bentonite 59.0% Example F Microemulsion Compound 2 1.0% triacetin 30.0% algayl glucoside of 8 to 10 carbon atoms 30.0% glyceryl monooleate 19.0% water 20.0% Example G Wettable powder Compound 9 65.0% dodecylphenol polietielnglycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0% Test results indicate that the compounds of the present invention are highly active herbicides both before and after germination and / or regulators of plant growth. Many of them have utility for the elimination of weeds before and / or after germination, of broad spectrum in areas where a complete elimination of all vegetation is desired such as around fuel storage tanks, industrial storage areas, lots parking, auto cinemas, airfields, river banks, irrigation and other waterways, around advertisements and structures of roads and trains. Many of the compounds of this invention, by virtue of their selective metabolism in crops versus weeds or by selective activity at the locus of physiological inhibition of crops and weeds or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective elimination of grass and broadleaf weeds within a crop / weed mixture. A person skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can be easily determined by performing systematic biological and / or biochemical tests. The compounds of this invention may show tolerance to important agronomic crops which include, but are not limited to alfalfa, barley, cotton, wheat, colsa, sugar beet, corn, sorghum, soy, rice, oatmeal, peanuts, vegetables, tomato , potatoes, harvests of perennial plants that include coffee, cocoa, palm oil, rubber, sugarcane, citrus, grapes, fruit trees, walnut trees, plantain, plantain, pineapple, hops, te and bosgue trees such as eucalyptus and conifers (for example, loblolly pine) and grass species (for example Kentucky blue weeds, St. Augustine grass, Kentucky cañuela and Bermuda grass). The compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, to express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin) and / or to express other useful bodies. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the present compounds are useful for modifying plant growth. Since the compounds of the invention have herbicidal activity before germination as well as after germination, for the elimination of unwanted vegetation by destruction or damage to vegetation or reduction of its growth, the compounds can be usefully applied for a variety of methods which involve contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a diluent, to the foliage or to another part of the unwanted vegetation or to the environment of the unwanted vegetation such as the soil or the vegetation. water in which the unwanted vegetation will grow or which surrounds the seed or other propagules of unwanted vegetation. A herbicidally effective amount of the compounds of this invention is determined by numerous factors. These factors include: selected formulation, method of application, amount and type of vegetation present, growth conditions, etc. In general, a herbicidally effective amount of the compounds of this invention is from about 0.0001 to 20 kg / ha with a preferred range of about 0.001 to 5 kg / ha and a more preferred range of about 0.004 to 3 kg / ha. A person skilled in the art can readily determine the herbicidally effective amount necessary for the desired level of weed control. The compounds of this invention can be used alone or in combination with other herbicides, insecticides and fungicides and other agricultural gum substances such as fertilizers. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species and suppress the proliferation of any resistant biotype. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for the removal of weeds: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidasulfuron, aminopyralide, amitrol, ammonium sulphamate, anilophos, asulam, atrazine, azimsulfuron, beflubutamide, benazoline, benazoline-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobiciclon, benzofenap, bifenox, bilanafos, bispiribac and its sodium salt, bromacil, bromobutide, bromophenoxy, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamiphos, butralin, butroxydim, butylate, cafenstrol, carbetamide, carfentrazone-ethyl, catechin, chloromethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazone, chlorimuron-ethyl, chlorotoluron, chloroprofan, chlorsulfuron, chlortal-dimethyl, chlortiamide, cinidon-ethyl, cinmetilin, cinosulfuron, clefoxidim, todim, clodinafop-propargyl, clomazone, clomeprop, clopyralide, clopyralide-olamine, cloransulam-methyl, copper sulfate, CUH-35 (2- [[[4-chloro-2-fluoro-5- [(1-methyl-2)] -propynyl) oxy] phenyl] (3-fluorobenzoyl) -amino] carbonyl] -l- "2-methoxyethyl-cyclohexen-l-carboxylate), cumyluron, cyanazine, cycloate, cyclo-sulfamuron, cycloxydim, cyhalofop-butyl, 2-4 D and its esters of butotyl, butyl, isoctyl and isopropyl and its salts of dimethylammonium, diolamine and trolamine, diamuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its salts of dimethylammonium, potassium and sodium, desmedipham, desmethrin , dicamba and its salts of diglucolamonium, dimethylammonium, potassium and sodium, diclobenil, diclorprop, diclofop-methyl, diclosulam, diphenyl diphenyl methacrylate, diflufenican, diflufenzopir, dimefuron, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimethenamid-P, dimetipine, dimethylarsinic acid and its sodium salt, dinitra ina, dinoterb, diphenamide, diguat dibromide, dithiopyr, diuron, DNOC, endo such, epoprodan, EPTC, esprocarb, ethalfluralin, etametsulfuron-methyl, etofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, flucloraline, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazine, fluometuron, fluoroglucofen- ethyl, flupirsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, Fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foransulfuron, fosamine-amino, glufosinate, glufosinate to onium, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including gue sesguisodio) and trimesium (of alternative way mentioned as sulfosate), halosulfuron-methyl, haloxifop-etotyl, haloxifop-methyl, hexazinone, HOK-201 (N- (2,4-difluorophenyl) -1,5-dihydro-N- (1-methylethyl) -5 -oxo-l- [(tetrahydro-2H-pyran-2-yl) -methyl] -4H- 1, 2,4-triazole-4-carboxamide), imazametabenz-methyl, imazamox, imazapic, imazapir, imazaguin, imazaguin- anaonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxinyl, ioxinyl actanoate, ioxinyl-sodium, isoproturon, isouron, isoxaben, isoxaflutole, isoxaclortol, isoxadifen, KUH-021 (N- [2- [(4 , 6-dimethoxy-2-pyrimidinyl) hydroxymethyl] -6- (methoxymethyl) phenyl] -1, 1-difluoro-methanesulfonamide), lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (for example MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium), esters (for example MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (for example MCPA-thioethyl), MCPB and their salts (for example MCPB-sodium ) and esters (eg MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium, metildimron, methobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, methoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, naphthalam, neburon, nicosulfuron, norflurazone, orbencarb, orizaline, oxadiargyl, oxadiazone, oxasulfuron , oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penosulam, pentanochlor, pentoxazone, perfluidone, petoxiamida, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primi sulfuron-methyl, prodiamine, profoxidim, prometone, prometrin, propachlor, propanil, propaguizafop, propazine, profam, propisoclor, propoxycarbazone, propoxycarbazone-sodium, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyrafluen-ethyl, pyrazogil, pyrazolate, pyrazolinate, pyrazoxifen, pyrazosulfuron-ethyl, piribenzoxin, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, guinclorac, guimerac, quinoclamine, quizalofop-ethyl, guizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tepraloxidin, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thifensulfuron-methyl, thiobencarb, tiocarbazil, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotilo, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, trisulfuron- methyl, tritosulfuron and vernolate. Other herbicides also include bioherbicides such as Alternarla destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini &Schweinitz) Dit: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub. Combinations of the compounds of the invention with other herbicides can result in a greater than additive (ie, synergistic) effect on weeds and / or a minor effect than additive (i.e., sanitizer) on crops or other desirable plants. In some cases, combinations with other herbicides having a similar elimination spectrum but a different mode of action will be particularly advantageous to prevent the development of resistant weeds. The effective herbicidal amounts of the compounds of the invention as well as the effective herbicidal amounts of other herbicides can be easily determined by a person skilled in the art by simple experimentation. They are preferred for a better elimination of unwanted vegetation (for example a lower use rate, a broader spectrum than controlled weeds or an increased crop safety) or to avoid the development of resistant meers, mixtures of a compound of this invention with a herbicide selected from the group consisting of diuron, hexazinone, terbacil, bromacil, glyphosate (particularly glyphosate-isopropylammonium, glyphosate-sodium, glyphosate-potassium, glyphosate-trimesium), glufosinate (particularly glufosinate-ammonium), azimsulfuron, chlorsulfuron, etametsulfuron-methyl, chlorimuron-ethyl, bensulfuron-methyl, rimsulfuron, sulfometuron-methyl, metsulfuron-methyl, nicosulfuron, tribenuron-methyl, trifensulfuron-methyl, flupirsulfuron-methyl, flupirsul-furon -methyl-sodium, halosulfuron-methyl, primisulfuron-methyl, trifloxysulfuron, foramsulfuron, mesosulfuron-methyl, iodosulfuron-methyl, isoproturon, ametrin, amitrol, paraquat dihydrochloride, dicuat dibromide, atrazine, metribuzin, acetochlor, metolachlor, S-metolachlor , alachlor, pretilachlor, sethoxydime, tralcoxidime, clethodima, cyhalofop-butyl, guizalofop-ethyl, diclofop-methyl, clodinafop-propargyl, fenoxaprop-ethyl, dimethenamid, flufenacet, picloram, prodiamine, fosamin-ammonium, 2, 4-D, 2 , 4-DB, dicamba, penoxsulam, flumetsulam, naptalam, pendimethalin, orizaline, MCPA (and its salts of dimethylammonium, potassium and sodium), MCPA-isoctyl, MCPA-thioethyl, mecoprop, clopyralide, aminopyralide, triclopir, fluroxipir, dif lufenzopyr, imazapir, imazetapir, imazamox, picolinafeno, oxyfluorfen, oxadiazon, carfentrazona-etil, sulfentrazona, flumioxazina, difluíenican, bromoxynil, propanil, thiobencarb, molinate, fluridone, mesotrione, sulcotrione, • isoxaflutol, isoxabeno, clomazona, anilofos, beflubutamida, benfuresato , bentazone, benzobicyclone, benzophenap, bromobutide, butachlor, butamiphos, cafenstrol, clomeprop, dimimetamide, dimethamine, daimuron, esprocarb, ethobenzanide, fentrazamide, indanofan, cumiluron, mefenacet, oxaziclomephone, oxadiargyl, pentoxazone, pyrazolonyl, pyrazolate, pyributicarb, piriftalide, piriminobac -methyl, tenilchlor, bispyribac-sodium, clefoxidim, copper sulfate, cyclosulfuron, cyclosulfamuron, ethoxysulfuron, epoprodan, flucetosulfuron, imazosulfuron, metamifop, pyrazosulfuron-ethyl, -guinclorac, flucarbazone-sodium, propoxycarbazone-sodium, amicarbazone, florasulam, triasulfuron, triaziflam, pinoxaden, tritosulfuron, amidosulfuron, metosulam, sulfosulfuron, piraflufen-ethyl , HOK-201, KUH-021 and CUH-35. Specifically preferred mixtures (the compound numbers refer to compounds in the index table A-D) are selected from the group: compound 4 and diuron; compound 9 and diuron; compound 58 and diuron; compound 64 and diuron; compound 65 (and salts thereof) and diuron; compound 94 and diuron; compound 95 (and salts thereof) and diuron; compound 96 and diuron; compound 135 (and salts thereof) and diuron; compound 4 and hexazinone; compound 9 and hexazinone; compound 58 and hexazinone; compound 64 and hexazinone; compound 65 (and salts thereof) and hexazinone; compound 94 and hexazinone; compound 95 (and salts thereof) and hexazinone; compound 96 and hexazinone; compound 135 (and salts thereof) and hexazinone; compound 4 and terbacil; compound 9 and terbacil; compound 58 and terbacil; compound 64 and terbacil; compound 65 (and salts thereof) and terbacil; compound 94 and terbacil; compound 95 (and salts thereof) and terbacil; compound 96 and terbacil; compound 135 (and salts thereof) and terbacyl; compound 4 and bromacil; compound 9 and bromacil; compound 58 and bromacil; compound 64 and bromacil; compound 65 (and salts thereof) and bromacil; compound 94 and bromacil; compound 95 (and salts thereof) and bromacil; compound 96 and bromacil; compound 135 (and salts thereof) and bromacil; compound 4 and glyphosate; compound 9 and glyphosate; compound - 58 and glyphosate; compound 64 and glyphosate; compound 65 (and salts thereof) and glyphosate; compound 94 and glyphosate; compound 95 (and salts thereof) and glyphosate; compound 96 and glyphosate; compound 135 (and salts thereof) and glyphosate; compound 4 and glufosinate; compound 9 and glufosinate; compound 58 and glufosinate; compound 64 and glufosinate; compound 65 (and salts thereof) and glufosinate; compound 94 and glufosinate; compound 95 (and salts thereof) and glufosinate; compound 96 and glufosinate; compound 135 (and salts thereof) and glufosinate; compound 4 and azimsulfuron; compound 9 and azimsulfuron; compound 58 and azimsulfuron; compound 64 and azimsulfuron; compound 65 (and salts thereof) and azimsulfuron; compound 94 and azimsulfuron; compound 95 (and salts thereof) and azimsulfuron; compound 96 and azimsulfuron; compound 135 (and salts thereof) and azimsulfuron; compound 4 and chlorsulfuron; compound 9 and chlorsulfuron; compound 58 and chlorsulfuron; compound 64 and chlorsulfan; compound 65 (and salts thereof) and chlorsulfuron; compound 94 and chlorsulfuron; compound 95 (and salts thereof) and chlorsulfuron; compound 96 and chlorsulfuron; compound 135 (and salts thereof) and chlorsulfuron; compound 4 and etametsufuron-methyl; compound 9 and etametsufuron-methyl; compound 58 and etametsufuron-methyl; compound 64 and etametsufuron-methyl; compound 65 (and salts thereof) and etametsufuron-methyl; compound 94 and etametsufuron-methyl; compound 95 (and salts thereof) and etametsufuron-methyl; compound 96 and etametsufuron-methyl; compound 135 (and salts thereof) and etametsufuron-methyl; compound 4 and chlorimuron-ethyl; compound 9 and chlorimuron-ethyl; compound 58 and chlorimuron-ethyl; compound 64 and chlorimuron-ethyl; compound 65 (and salts thereof) and chlorimuron-ethyl; compound 94 and chlorimuron-ethyl; compound 95 (and salts thereof) and chlorimuron-ethyl; compound 96 and chlorimuron-ethyl; compound 135 (and salts thereof) and chlorimuron-ethyl; compound 4 and bensulfuron-methyl; compound 9 and bensulfuron-methyl; compound 58 and bensulfuron-methyl; compound 64 and bensulfuron-methyl; compound 65 (and salts thereof) and bensulfuron-methyl; compound 94 and bensulfuron-methyl; compound 95 (and salts thereof) and bensulfuron-methyl; compound 96 and bensulfuron-methyl; compound 135 (and salts thereof) and bensulfuron-methyl; compound 4 and rimsulfuron; compound 9 and rimsulfuron; compound 58 and rimsulfuron; compound 64 and rimsulfuron; compound 65 (and salts thereof) and rimsulfuron; compound 94 and rimsulfuron; compound 95 (and salts thereof) and rimsulfuron; compound 96 and rimsulfaron; compound 135 (and salts thereof) and rimsulfuron; compound 4 and sulfometuron-methyl; compound 9 and sulfometuron-methyl; compound 58 and sulfometuron-methyl; compound 64 and sulfometuron-methyl; compound 65 (and salts thereof) and sulfometuron-methyl; compound 94 and sulfometuron-methyl; compound 95 (and salts thereof) and sulfometuron-methyl; compound 96 and sulfometuron-methyl; compound 135 (and salts thereof) and sulfometuron-methyl; compound 4 and metsulfuron-methyl; compound 9 and metsulfuron-methyl; compound 58 and metsulfuron-methyl; compound 64 and metsulfuron-methyl; compound 65 (and salts thereof) and metsulfuron-methyl; compound 94 and metsulfuron-methyl; compound 95 (and salts thereof) and methosulfan-methyl; compound 96 and methosulfan-methyl; compound 135 (and salts thereof) and metsulfuron-methyl; compound 4 and nicosulfuron; compound 9 and nicosulfuron; compound 58 and nicosulfuron; compound 64 and nicosulfuron; compound 65 (and salts thereof) and nicosulfuron; compound 94 and nicosulfuron; compound 95 (and salts thereof) and nicosulfuron; compound 96 and nicosulfuron; compound 135 (and salts thereof) and nicosulfuron; compound 4 and tribenuron-methyl; compound 9 and tribenuron-methyl; compound 58 and tribenuron-methyl; compound 64 and tribenuron-methyl; compound 65 (and salts thereof) and tribenuron-methyl; compound 94 and tribenuron-methyl; compound 95 (and salts thereof) and tribenuron-methyl; compound 96 and tribenuron-methyl; compound 135 (and salts thereof) and tribenuron-methyl; compound 4 and thifensulfuron-methyl; compound 9 and tifensulfuron-methyl; compound 58 and tifensulfuron-methyl; compound 64 and thifensulfuron-methyl; compound 65 (and salts thereof) and thifensulfuron-methyl; compound 94 and tifensulfuron-methyl; compound 95 (and salts thereof) and thifensulfuron-methyl; compound 96 and thifensulfuron-methyl; compound 135 (and salts thereof) and thifensulfuron-methyl; compound 4 and flupirsulfuron-methyl; compound 9 and flupirsulfuron-methyl; compound 58 and flupirsulfuron-methyl; compound 64 and flupirsulfuron-methyl; compound 65 (and salts thereof) and flupirsulfuron-methyl; compound 94 and flupirsulfuron-methyl; compound 95 (and salts thereof) and flupirsulfuron-methyl; compound 96 and flupirsulfuron-methyl; compound 135 (and salts thereof) and flupirsulfuron-methyl; compound 4 and flupirsulfuron-methyl-sodium; compound 9 and flupyrsulfuron-methyl-sodium; compound 58 and flupirsulfuron-methyl-sodium; compound 64 and flupyrsulfuron-methyl-sodium; compound 65 (and salts thereof) and flupirsulfuron-methyl sodium; compound 94 and flupirsulfuron-methyl-sodium; compound 95 (and salts thereof) and flupirsulfuron-methyl-sodyl; compound 96 flupylsulfuron-methyl-sodium; compound 135 (and salts thereof) and flupirsulfuron-methyl-sodium; compound 4 and halosulfuron-methyl; compound 9 and halosulfuron-methyl; compound 58 and halosulfuron-methyl; compound 64 and halosulfuron-methyl; compound 65 (and salts thereof) and halosulfuron-methyl; compound 94 and halosulfuron-methyl; compound 95 (and salts thereof) and halosulfuron-methyl; compound 96 and halosulfuron-methyl; compound 135 (and salts thereof) and halosulfuron-methyl; compound 4 and primisulfuron-methyl; compound 9 and primisulfuron-methyl; compound 58 and primisulfuron-methyl; compound 64 and primisulfuron-methyl; compound 65 (and salts thereof) and primisulfuron-methyl; compound 94 and primisulfuron-methyl; compound 95 (and salts thereof) and primisulfaron-methyl; compound 96 and primisulfuron-methyl; compound 135 (and salts thereof) and primisulfuron-methyl; compound 4 and trifloxysulfuron; compound 9 and trifloxysulfuron; compound 58 and trifloxysulfuron; compound 64 and trifloxysulfuron; compound 65 (and salts thereof) and trifloxysulfuron; compound 94 and trifloxysulfuron; compound 95 (and salts thereof) and trifloxysulfuron; compound 96 and trifloxysulfuron; compound 135 (and salts thereof) and trifloxysulfuron; compound 4 and foramsulfuron; compound 9 and foramsulfuron; compound 58 and foramsulfaron; compound 64 and foramsulfuron; compound 65 (and salts thereof) and foramsulfuron; compound 94 and foramsulfuron; compound 95 (and salts thereof) and foramsulfuron; compound 96 and foramsulfuron; compound 135 (and salts thereof) and foramsulfuron; compound 4 and mesosulfuron-methyl; compound 9 and mesosulfuron-methyl; compound 58 and mesosulfuron-methyl; compound 64 and mesosulfuron-methyl; compound 65 (and salts thereof) and mesosulfuron-methyl; compound 94 and mesosulfuron-methyl; compound 95 (and salts thereof) and mesosulfuron-methyl; compound 96 and mesosulfuron-methyl; compound 135 (and salts thereof) and mesosulfuron-methyl; compound 4 and yodosulfuron-methyl; compound 9 and iodosulfan-methyl; compound 58 and yodosulfuron-methyl; compound 64 and yodosulfuron-methyl; compound 65 (and salts thereof) and yodosulfaron-methyl; compound 94 and yodosulfuron-methyl; compound 95 (and salts thereof) and iodosulfuron-methyl; compound 96 and yodosulfuron-methyl; compound 135 (and salts thereof) and yodosulfuron-methyl; compound 4 and isoproturon; compound 9 and isoproturon; "Compound 58 and isoproturon; compound 64 and isoproturon; compound 65 (and salts thereof) and isoproturon; compound 94 and isoproturon; compound 95 (and salts thereof) and isoproturon; compound 96 and isoproturon; compound 135 (and salts thereof) and isoproturon; compound 4 and ametrin; compound 9 and ametrin; compound 58 and ametrin; compound 64 and ametrin; compound 65 (and salts thereof) and ametryn; compound 94 and ametryn; compound 95 (and salts thereof) and ametryn; compound 96 and ametrin; compound 135 (and salts thereof) and ametryn; compound 4 and amitrol; compound 9 and amitrol; compound 58 and amitrol; compound 64 and amitrol; compound 65 (and salts thereof) and amitrol; compound 94 and amitrol; compound 95 (and salts thereof) and amitrol; compound 96 and amitrol; compound 135 (and salts thereof) and amitrol; compound 4 and paraquat dichloride; compound 9 and paraquat dichloride; compound 58 and paraquat dichloride; compound 64 and paraquat dichloride; compound 65 (and salts thereof) and paraquat dichloride; compound 94 and paraquat dichloride; compound 95 (and salts thereof) and paraquat dichloride; compound 96 and paraquat dichloride; compound 135 (and salts thereof) and paraquat dichloride; compound 4 and dicuat dibromide; compound 9 and dicouat dibromide; compound 58 and dicouat dibromide; compound 64 and dicuat dibromide; compound 65 (and salts thereof) and dicuat dibromide; compound 94 and dicuat dibromide; compound 95 (and salts thereof) and dicuat dibromide; compound 96 and dicouat dibromide; compound 135 (and salts thereof) and dicuat dibromide; compound 4 and atrazine; compound 9 and atrazine; compound 58 and atrazine; compound 64 and atrazine; compound 65 (and salts thereof) and atrazine; compound 94 and atrazine; compound 95 (and salts thereof) and atrazine; compound 96 and atrazine; compound 135 (and salts thereof) and atrazine; compound 4 and metribuzin; compound 9 and metribuzin; compound 58 and metribuzin; compound 64 and metribuzin; compound 65 (and salts thereof) and metribuzin; compound 94 and metribuzin, compound 95 (and salts thereof) and metribuzin; compound 96 and metribuzin; compound 135 (and salts thereof) and metribuzin; compound 4 and acetochlor; compound 9 and acetochlor; compound 58 and acetochlor; compound 64 and acetochlor; compound 65 (and salts thereof) and acetochlor; compound 94 and acetochlor; compound 95 (and salts thereof) and acetochlor; compound 96 and acetochlor; compound 135 (and salts thereof) and acetochlor; compound 4 and metolachlor; compound 9 and metolachlor; compound 58 and metolachlor; compound 64 and metolachlor; compound 65 (and salts thereof) and metolachlor; compound 94 and metolachlor; compound 95 (and salts thereof) and metolachlor; compound 96 and metolachlor; compound 135 (and salts thereof) and metolachlor; compound 4 and S-metolachlor; compound 9 and S-metolachlor; compound 58 and S-metolachlor; compound 64 and S-metolachlor; compound 65 (and salts thereof) and S-metolachlor; compound 94 and S-metolachlor; compound 95 (and salts thereof) and S-metolachlor, compound 96 and S-metolachlor; compound 135 (and salts thereof) and S-metolachlor; compound 4 and alachlor; compound 9 and alachlor; compound 58 and alachlor; compound 64 and alachlor; compound 65 (and salts thereof) and alachlor; compound 94 and alachlor; compound 95 (and salts thereof) and alachlor; compound 96 and alachlor; compound 135 (and salts thereof) and alachlor; compound 4 and pretilachlor; compound 9 and pretilachlor; compound 58 and pretilachlor; compound 64 and pretilachlor; compound 65 (and salts thereof) and pretilachlor, compound 94 and pretilachlor; compound 95 (and salts thereof) and pretilachlor; compound 96 and pretilachlor; compound 135 (and salts thereof) and pretilachlor; compound 4 and sethoxydim; compound 9 and sethoxydim; compound 58 and sethoxydim; compound 64 and sethoxydim; compound 65 (and salts thereof) and sethoxydim; compound 94 and sethoxydim, compound 95. (and salts thereof) and sethoxydim; compound 96 and sethoxydim; compound 135 (and salts thereof) and sethoxydim; compound 4 and tralcoxidim; compound 9 and tralcoxidim; compound 58 and tralcoxidim; compound 64 and tralcoxidim; compound 65 (and salts thereof) and tralcoxydim; compound 94 and tralcoxidim; compound 95 (and salts thereof) and tralcoxidim; compound 96 and tralcoxidim; compound 135 (and salts thereof) and tralcoxydim; compound 4 and clethodim; compound 9 and clethodim; compound 58 and clethodim; compound 64 and cietodim; compound 65 (and salts thereof) and clethodim; compound 94 and clethodim; compound 95 (and salts thereof) and clethodim; compound 96 and clethodim; compound 135 (and salts thereof) and clethodim; compound 4 and cyhalofop-butyl; compound 9 and cyhalofop-butyl; compound 58 and cyhalofop-butyl; compound 64 and cyhalofop-butyl; compound 65 (and salts thereof) and cyhalofop-butyl; compound 94 and cyhalofop-butyl; compound 95 (and salts thereof) and cyhalofop-butyl; compound 96 and cyhalofop-butyl; compound 135 (and salts thereof) and cyhalofop-butyl; compound 4 and guizalofop-ethyl; compound 9 and guizalofop-ethyl; compound 58 and guizalofop-ethyl; compound 64 and guizalofop-ethyl; compound 65 (and salts thereof) and guizalofop-ethyl; compound 94 and guizalofop-ethyl; compound 95 (and salts thereof) and guizalofop-ethyl; compound 96 and guizalofop-ethyl; compound 135 (and salts thereof) and guizalofop-ethyl; compound 4 and diclofop-methyl; compound 9 and diclofop-methyl; compound 58 and diclofop-methyl; compound 64 and diclofop-methyl; compound 65 (and salts thereof) and diclofop-ethyl; compound 94 and diclofop-methyl; compound 95 (and salts thereof) and diclofop-methyl; compound 96 and diclofop-methyl; compound 135 (and salts thereof) and diclofop-methyl; compound 4 and clodinafop-propargyl; compound 9 and clodinafop-propargyl; compound 58 and clodinafop-propargyl; compound 64 and clodinafop-propargyl; compound 65 (and salts thereof) and clodinafop-propargyl; compound 94 and clodinafop-propargyl; compound 95 (and salts thereof) and clodinafop-propargyl; compound 96 and clodinafop-propargyl; compound 135 (and salts thereof) and clodinafop-propargyl; compound 4 and fenoxaprop-ethyl; compound 9 and fenoxaprop-ethyl; compound 58 and fenoxaprop-ethyl; compound 64 and fenoxaprop-ethyl; compound 65 (and salts thereof) and fenoxaprop-ethyl; compound 94 and fenoxaprop-ethyl; compound 95 (and salts thereof) and fenoxaprop-ethyl; compound 96 and fenoxaprop-ethyl; compound 135 (and salts thereof) and fanoxaprop-ethyl; compound 4 and dimethenamide; compound 9 and dimethenamide; compound 58 and dimethenamide; compound 64 and dimethenamid; compound 65 (and salts thereof) and dimethenamide; compound 94 and dimethenamide; compound 95 (and salts thereof) and dimethenamid; compound 96 and dimethenamide; compound 135 (and salts thereof) and dimethenamide; compound 4 and flufenacet, compound 9 and flufenacet, compound 58 and flufenacet; compound 64 and flufenacet; compound 65 (and salts thereof) and flufenacet; compound, 94 and flufenacet; compound 95 (and salts thereof) and flufenacet; compound 96 and flufenacet; compound 135 (and salts thereof) and flufenacet; compound 4 and picloram; compound 9 and picloram; compound 58 and picloram; compound 64 and picloram; compound 65 (and salts thereof) and picloram; compound 94 and picloram; compound 95 (and salts thereof) and picloram; compound 96 and picloram; compound 135 (and salts thereof) and picloram; compound 4 and prodiamine; compound 9 and prodiamine; compound 58 and prodiamine; compound 64 and prodiamine; compound 65 (and salts thereof) and prodiamine; compound 94 and prodimin; compound 95 (and salts thereof) and prodiamine; compound 96 and prodiamine; compound 135 (and salts thereof) and prodiamine; compound 4 and fosamine-ammonium; compound 9 and fosamine-ammonium; compound 58 and fosamine-ammonium; compound 64 and fosamine-ammonium; compound 65 (and salts thereof) and fosamine-ammonium; compound 94 and fosamine-ammonium; compound 95 (and salts thereof) and fosamine-ammonium; compound 96 and fosamine-ammonium; compound 135 (and salts thereof) and fosamine-ammonium; compound 4 and 2, 4-D; compound 9 and 2,4-D; compound 58 and 2,4-D; compound 64 and 2,4-D; compound 65 (and salts thereof) and 2,4-D; compound 94 and 2,4-D; compound 95 (and salts thereof) and 2,4-D; compound 96 and 2,4-D; compound 135 (and salts thereof) and 2,4-D; compound 4 and 2,4-DB; compound 9 and 2,4-DB; compound 58 and 2,4-DB; compound 64 and 2,4-DB; compound 65 (and salts thereof) and 2,4-DB; compound 94 and 2,4-DB; compound 95 (and salts thereof) and 2,4-DB; compound 96 and 2,4-DB; compound 135 (and salts thereof) and 2,4-DB; compound 4 and dicamba; compound 9 and dicamba; compound 58 and dicambá; compound 64 and dicamba; compound 65 (and salts thereof) and dicamba; compound 94 and dicamba; compound 95 (and salts thereof) and dicamba; compound 96 and dicamba; compound 135 (and salts thereof) and dicamba; compound 4 and penoxsulam; compound 9 and penoxsulam; compound 58 and penoxsulam; compound 64 and penoxsulam; compound 65 (and salts thereof) and penoxsulam; compound 94 and penoxsulam; compound 95 (and salts thereof) and penoxsulam; compound 96 and penoxsulam; compound 135 (and salts thereof) and penoxsulam; compound 4 and flumetsulam; compound 9 and flumetsulam; compound 58 and flumetsulam; compound 64 and flumetsulam; compound 65 (and salts thereof) and flumetsulam; compound 94 and flumetsulam; compound 95 (and salts thereof) and flumetsulam; compound 96 and flumetsulam; compound 135 (and salts thereof) and flumetsulam; compound 4 and naptalam; compound 9 and naptalam; compound 58 and naptalam; compound 64 and naptalam; compound 65 (and salts thereof) and naptalam; compound 94 and naptalam; compound 95 (and salts thereof) and naptalam; compound 96 and naptalam; compound 135 (and salts thereof) and naptalam; compound 4 and pendimethalin; compound 9 and pendimethalin; compound 58 and pendimethalin; compound 64 and pendimethalin; compound 65 (and salts thereof) and pendimethalin; compound 94 and pendimethalin; compound 95 (and salts thereof) and pendimethalin; compound 96 and pehdimethalin; compound 135 (and salts thereof) and pendimethalin; compound 4 and oryzalin; compound 9 and oryzalin; compound 58 and oryzalin; compound 64 and oryzalin; compound 65 (and salts thereof) and oryzalin; compound 94 and oryzalin; compound 95 (and salts thereof) and oryzalin; compound 96 and oryzalin; compound 135 (and salts thereof) and oryzalin; compound 4 and MCPA (and salts (thio) esters thereof); compound 9 and MCPA (and salts (uncle) esters thereof); compound 58 and MCPA (and salts (uncle) esters thereof); compound 64 and MCPA (and salts (uncle) esters thereof); compound 65 (and salts thereof) and MCPA. (and salts (thio) esters thereof); compound 94 and MCPA (and salts (thio) esters thereof); compound 95 (and salts (thio) esters thereof) and MCPA (and salts (thio) esters thereof); compound 96 and MCPA (and salts (thio) esters thereof); compound 135 (and salts thereof) and MCPA (and salts (thio) esters thereof); compound 4 and mecoprop; compound 9 and mecoprop; compound 58 and mecoprop; compound 64 and mecoprop; compound 65 (and salts thereof) and mecoprop; compound 94 and mecoprop; compound 95 (and salts thereof) and mecoprop; compound 96 and mecoprop; compound 135 (and salts of the same) and mecopropyl, compound 4 and clopyralid, compound 9 and clopyralid, compound 58 and clopyralid; compound 64 and clopyralid; compound 65 (and salts thereof) and clopyralid; compound 94 and clopyralid; compound 95 (and salts thereof) and clopyralid; compound 90 and clopyralid; compound 135 (and salts thereof) and clopyralid; Compound 4 and aminopyralid; compound 9 and aminopyralid; compound 58 and aminopyralid; compound 64 and aminopyralid; compound 65 (and salts thereof) and aminopyralid, compound 94 and aminopyralid, compound 95 (and salts thereof) and aminopyralid, compound 96 and aminopyralid, compound 135 (and salts thereof) and aminopyralid; and triclopyr, compound 9 and triclopyr, compound 58 and triclopyr, compound 64 and triclopyr, compound 65 (and salts thereof) and triclopyr, compound 94 and triclopyr, compound 95 (and salts thereof) and triclopyr, compound 96 and triclopir, compound 135 (and salts thereof) and triclopyr; compound 4 and fluroxypyr; compound 9 and fluroxypyr; compound 58 and fluroxypyr; compound 64 and fluroxypyr; compound 65 (and salts thereof) and fluroxypyr; compound 94 and fluroxypyr; compound 95 (and salts thereof) and fluroxypyr; compound 96 and fluroxypyr; compound 135 (and salts thereof) and fluroxypyr; compound 4 and diflufenzopyr; compound 9 and diflufenzopyr; compound 58 and difluienzopyr, compound 64 and diflufenzopyr; compound 65 (and salts thereof) and diflufenzopyr; compound 94 and diflufenzopyr; compound 95 (and salts thereof) and diflufenzopyr; compound 96 and diflufenzopyr; compound 135 (and salts thereof) and diflufenzopyr; compound 4 and imazapyr; compound 9 and imazapyr; compound 58 and imazapyr; compound 64 and imazapyr; compound 65 (and salts thereof) and imazapyr; compound 94 and imazapyr; compound 95 (and salts thereof) and imazapyr; compound 96 and imazapyr; compound 135 (and "salts thereof) and imazapyr; compound 4 and imazetapyr; compound 9 and imazetapyr; compound 58 and imazetapyr; compound 64 and imazetapyr; compound 65 (and salts thereof) and imazetapyr; compound 94 and imazetapyr; compound 95 (and salts thereof) and imazetapyr; compound 96 and imazetapyr; compound 135 (and salts thereof) and imazetapyr; compound 4 and imazamox; compound 9 and imazamox; compound 58 and imazamox; compound 64 and imazamox; compound 65 (and salts thereof) and imazamox; compound 94 and imazamox; compound 95 (and salts thereof) and imazamox; compound 96 and imazamox; compound 135 (and salts thereof) and imazamox; compound 4 and picolinafen; compound 9 and picolinafen; compound 58 and picolinafen; compound 64 and picolinafen; compound 65 (and salts thereof) and picolinafen; compound 94 and picolinafen; compound 95 (and salts thereof) and picolinafen; compound 96 and picolinafen; compound 135 (and salts thereof) and picolinafen; compound 4 and oxyfluorfen; compound 9 and oxyfluorfen; compound 58 and oxyfluorfen; compound 64 and oxyfluorfen; compound 65 (and salts thereof) and oxyfluorfen; compound 94 and oxyfluorfen; compound 95 (and salts thereof) and oxyfluorfen; compound 96 and oxyfluorfen; compound 135 (and salts thereof) and oxyfluorfen; compound 4 and oxadiazon; compound 9 and oxadiazon; compound 58 and oxadiazon; compound 64 and oxadiazon; compound 65 (and salts thereof) and oxadiazon; compound 94 and oxadiazon; compound 95 (and salts thereof) and oxadiazon; compound 96 and oxadiazon; compound 135 (and salts thereof) and oxadiazon; compound 4 and carfentrazone-ethyl; compound 9 and carfentrazone-ethyl; compound 58 and carfentrazone-ethyl; compound 64 and carfentrazone-ethyl; compound 65 (and salts thereof) and carfentrazone-ethyl; compound 94 and carfentrazone-ethyl; compound 95 (and salts thereof) and carfentrazone-ethyl; compound 96 and carfentrazone-ethyl; compound 135 (and salts thereof) and carfentrazone-ethyl; compound 4 and sulfentrazone; compound 9 and sulfentrazone; compound 58 and sulfentrazone; compound 64 and sulfentrazone; compound 65 (and salts thereof) and sulfentrazone; compound 94 and sulfentrazone; compound 95 (and salts thereof) and sulfentrazone; compound 96 and sulfentrazone; compound 135 (and salts thereof) and sulfentrazone; compound 4 and flumioxazine; compound 9 and flumioxazine; compound 58 and flumioxazine; compound 64 and flumioxazine; compound 65 (and salts thereof) and flumioxazine; compound 94 and flumioxazine; compound 95 (and salts thereof) and flumioxazine; compound 96 and flumioxazine; compound 135 (and salts thereof) and flumioxazine; compound 4 and diflufenican; compound 9 and diflufenican; compound 58 and diflufenican; compound 64 and diflufenican; compound 65 (and salts thereof) and diflufenican; compound 94 and diflufenican; compound 95 (and salts thereof) and diflufenican; compound 96 and diflufenican; compound 135 (and salts thereof) and diflufenican; compound 4 and bromoxynil; compound 9 and bromoxynil; compound 58 and bromoxynil; compound 64 and bromoxynil; . compound 65 (and salts thereof) and bromoxynil; compound 94 and bromoxynil; compound 95 (and salts thereof) and bromoxynil; compound 96 and bromoxynil; compound 135 (and salts thereof) and bromoxynil; compound 4 and propanil; compound 9 and propanil; compound 58 and propanil; compound 64 and propanil; compound 65 (and salts thereof) and propanil; compound 94 and propanil; compound 95 (and salts thereof) and propanil; compound 96 and propanil; compound 135 (and salts thereof) and propanil; compound 4 and thiobencarb; compound 9 and thiobencarb; compound 58 and thiobencarb; compound 64 and thiobencarb; compound 65 (and salts thereof) and thiobencarb; compound 94 and thiobencarb; compound 95 (and salts thereof) and thiobencarb; compound 96 and thiobencarb; compound 135 (and salts thereof) and thiobencarb; compound 4 and fluridone; compound 9 and fluridone; compound 58 and fluridone; compound 64 and fluridone; compound 65 (and salts thereof) and fluridone; compound 94 and fluridone; compound 95 (and salts thereof) and fluridone; compound 96 and fluridone; compound 135 (and salts thereof) and fluridone; compound 4 and mesotrione; compound 9 and mesotrione; compound 58 and mesotrione; compound 64 and mesotrione; compound 65 (and salts thereof) and mesotrione; compound 94 and mesotrione; compound 95 (and salts thereof) and mesotrione; compound 96 and mosotrione; compound 135 (and salts thereof) and mesotrione; compound 4 and sulcotrione; compound 9 and sulcotrione; compound 58 and sulcotrione; compound 64 and sulcotrione; compound 65 (and salts thereof) and sulcotrione; compound 94 and sulcotrione; compound 95 (and salts thereof) and sulcotrione; compound 96 and sulcotrione; compound 135 (and salts thereof) and sulcotrione; compound 4 and isoxaflutole; compound 9 and isoxaflutole; compound 58 and isoxaflutole; compound 64 and isoxaflutole; compound 65 (and salts thereof) and isoxaflutole; compound 94 and isoxaflutole; compound 95 (and salts thereof) and isoxaflutole; compound 96 and isoxaflutole; compound 135 (and salts thereof) 'and isoxaflutole; compound 4 and isoxaben; compound 9 and isoxaben; compound 58 and isoxaben; compound 64 and isoxaben; compound 65 (and salts thereof) and isoxaben; compound 94 and isoxaben; compound 95 (and salts thereof) and isoxaben; compound 96 and isoxaben; compound 135 (and salts thereof) and isoxaben; compound 4 and clomazone; compound 9 and clomazone; compound 58 and clomazone; compound 64 and clomazone; compound 65 (and salts thereof) and clomazone; compound 94 and clomazone; compound 95 (and salts thereof) and clomazone; compound 96 and clomazone; compound 135 (and salts thereof) and clomazone; compound 4 and beflubutamide; compound 9 and beflubutamide; compound 58, and beflubutamide; compound 64 and beflubutamide; compound 65 (and salts thereof) and beflubutamide; compound 94 and beflubutamide; compound 95 (and salts thereof) and beflubutamide; compound 96 and beflubutamide; compound 135 (and salts thereof) and beflubutamide; compound 4 and benfuresate; compound 9 and benfuresate; compound 58 and benfuresate; compound 64 and benfuresate; compound 65 (and salts thereof) and benfuresate; compound 94 and benfuresate, compound 95 (and salts thereof) and benfuresate; compound 96 and benfuresate; compound 135 (and salts thereof) and benfuresate; compound 4 and bentazone; compound 9 and bentazone; compound 58 and bentazone; compound 64 and bentazone; compound 65 (and salts thereof) and bentazone; compound 94 and bentazone; compound 95 (and salts thereof) and bentazone; compound 96 and bentazone; compound 135 (and salts thereof) and bentazone; compound 4 and benzobicyclone; compound 9 and benzobicyclone; compound 58 and benzobicyclone; compound 64 and benzobicyclone; compound 65 (and salts thereof) and benzobicyclone; compound 94 and benzobicyclone; compound 95 (and salts thereof) and benzobicyclone; compound 96 and benzobicyclone; compound 135 (and salts thereof) and benzobicyclone; compound 4- and benzophenap; compound 9 and benzophenap; compound 58 and benzophenap; compound 64 and benzophenap; compound 65 (and salts thereof) and benzophenap; compound 94 and benzophenap; compound 95 (and salts thereof) and benzophenap; compound 96 and benzophenap; compound 135 (and salts thereof) and benzophenap; compound 4 and bromobutide; 9 'compound and bromobutide; compound 58 and bromobutide; compound 64 and bromobutide; compound 65 (and salts thereof) and bromobutide; compound 94 and bromobutide; compound 95 (and salts thereof) and bromobutide; compound 96 and bromobutide; compound 135 (and salts thereof) and bromobutide; compound 4 and butachlor; compound 9 and butachlor; compound 58 and butachlor; compound 64 and butachlor; compound 65 (and salts thereof) and butachlor; compound 94 and butachlor; compound 95 (and salts thereof) and butachlor; compound 96 and butachlor; compound 135 (and salts thereof) and butachlor; compound 4 and cafenstrol; compound 9 and cafenstrol; compound 58 and cafenstrol; compound 64 and cafenstrol; compound 65 (and salts thereof) and cafenstrol; compound 94 and cafenstrol; compound 95 (and salts thereof) and cafenstrol; compound 96 and cafenstrol; compound 135 (and salts thereof) and cafenstrol; compound 4 and clomeprop; compound 9 and clomeprop, compound 58 and clomeprop; compound 64 and clomeprop; compound 65 (and salts thereof) and clomeprop; compound 94 and clomeprop; compound 95 (and salts thereof) and clomeprop; compound 96 and clomeprop; compound 135 (and salts thereof) and clomeprop; compound 4 and dimethoperate; compound 9 and dimethoperate; compound 58 and dimethoperate; compound 64 and dimethoperate; compound 65 (and salts thereof) and dimepiperate; compound 94 and dimethoperate; compound 95 (and salts thereof) and dimepiperate, compound 96 and dimepiperate, compound 135 (and salts thereof) and dimepiperate, compound 4 and dimethamethrin; compound 9 and dimethamethrin; compound 58, and dimethamethrin; compound 64 and dimethamethrin; compound 65 (and salts thereof) and dimethamethrin; compound 94 and dimethamethrin; compound 95 (and salts thereof) and dimethamethrin; compound 96 and dimethamethrin; compound 135 (and salts thereof) and dimethamethrin; compound 4 and diamuron; compound 9 and diamuron; compound 58 and diamuron; compound 64 and diamuron; compound 65 (and salts thereof) and diamuron; compound 94 and diamuron; compound 95 (and salts thereof) and diamuron; compound 96 and diamuron; compound 135 (and salts thereof) and diamuron; compound 4 and esprocarb; compound 9 and esprocarb; compound 58 and esprocarb; compound 64 and esprocarb; compound 65 (and salts thereof) and esprocarb; compound 94 and esprocarb; compound 95 (and salts thereof) and esprocarb; compound 96 and esprocarb; compound 135 (and salts thereof) and esprocarb; compound 4 and etobenzanide; compound 9 and etobenzanide; compound 58 and etobenzanide; compound 64 and etobenzanide; compound 65 (and salts thereof) and etobenzanide; compound 94 and etobenzanide; compound 95 (and salts thereof) and etobenzanide; compound 96 and etobenzanide; compound 135 (and salts thereof) and etobenzanide; compound 4 and fentrazamid; compound 9 and fentrazamid; compound 58 and fentrazamid; compound 64 and fentrazamid; compound 65 (and salts thereof) and fentrazamid; compound 94 and fentrazamid; compound 95 (and salts thereof) and phentrazamid; compound 96 and fentrazamid; compound 135 (and salts thereof) and phentrazamid; compound 4 and indanofan; compound 9 and indanofan; compound 58 and indanofan; compound 64 and indanofan; compound 65 (and salts thereof) and indanofan; compound 94 and indanofan; compound 95 (and salts thereof) and indanofan; compound 96 and indanofan; compound 135 (and salts thereof) and indanofan; compound 4 and cumyluron; compound 9 and cumyluron; compound 58 and cumyluron; compound 64 and cumyluron; compound 65 (and salts thereof) and cumyluron, compound 94 and cumyluron; compound 95 (and salts thereof) and cumyluron; compound 96 and cumiluron; compound 135 (and salts thereof) and cumiluron; compound 4 and mefenacet; compound 9 and mefenacet; compound 58 and mefenacet; compound 64 and mefenacet; compound 65 (and salts thereof) and mefenacet; compound 94 and mefenacet; compound 95 (and salts thereof) and mefenacet; compound 96 and mefenacet; compound 135 (and salts thereof) and mefenacet; compound 4 and oxaziclomene; compound 9 and oxaziclomene; compound 58 and oxaziclomene; compound 64 and oxaziclomene; compound 65 (and salts thereof) and oxaziclomene; compound 94 and oxaziclomefone; compound 95 (and salts thereof) and oxaziclomefone; compound 96 and oxaziclomene; compound 135 (and salts thereof) and oxaziclomefone; compound 4 and oxadiargyl; compound 9 and oxadiargyl; compound 58 and oxadiargyl; compound 64 and oxadiargyl; compound 65 (and salts thereof) and oxadiargyl; compound 94 and oxadiargyl; compound 95 (and salts thereof) and oxadiargyl; compound 96 and oxadiargyl; compound 135 (and salts thereof) and oxadiargyl; compound 4 and pentoxazone; compound 9 and pentoxazone; compound 58 and pentoxazone; compound 64 and pentoxazone; compound 65 (and salts thereof) and pentoxazone; compound 94 and pentoxazone; compound 95 (and salts thereof) and pentoxazone; compound 96 and pentoxazone; compound 135 (and salts thereof) and pentoxazone; compound 4 and pyraclonil; compound 9 and pyraclonil; compound 58 and pyraclonil; compound 64 and pyraclonil; compound 65 (and salts thereof) and pyrazolonyl; compound 94 and pyraclonyl; compound 95 (and salts thereof) and pyrazolonyl; compound 96 and pyraclonil; compound 135 (and salts thereof) and pyrazolonyl; compound 4 and pyrazolate; compound 9 and pyrazolate; compound 58 and pyrazolate; compound 64 and pyrazolate; compound 65 (and salts thereof) and pyrazolate; compound 94 and pyrazolate; compound 95 (and salts thereof) and pyrazolate; compound 96 and pyrazolate; compound 135 (and salts thereof) and pyrazolate; compound 4 and pyributicarb; compound 9 and pyributicarb; compound 58 and pyributicarb; compound 64 and pyributicarb; compound 65 (and salts thereof) and pyributicarb; compound 94 and pyributicarb; compound 95 (and salts thereof) and pyributicarb; compound 96 and pyributicarb; compound 135 (and salts thereof) and pyributicarb; compound 4 and piriftalide; compound 9 and piriftalide; compound 58 and piriftalide; compound 64 and piriftalide; compound 65 (and salts thereof) and piriftalide; compound 94 and piriftalide; compound 95 (and salts thereof) and piriftalide; compound 96 and piriftalide; compound 135 '(and salts thereof) and piriftalide; compound 4 and piriminobac-methyl; compound 9 and piriminobac-methyl; compound 58 and piriminobac-methyl; compound 64 and piriminobac-methyl; compound 65 (and salts thereof) and piriminobac-methyl; compound 94 and piriminobac-methyl; compound 95 (and salts thereof) and piriminobac-methyl; compound 96 and piriminobac-methyl; compound 135 (and salts thereof) and piriminobac-methyl; compound 4 and tenylchlor; compound 9 and tenylchlor; compound 58 and tenylchlor; compound 64 and tenylchlor; compound 65 (and salts thereof) and tenylchlor; compound 94 and tenylchlor; compound 95 (and salts thereof) and tenylchlor; compound 96 and tenylchlor; compound 135 (and salts thereof) and tenylchlor; compound 4 and bispyribac-sodium; compound 9 and bispyribac-sodium; compound 58 and bispyribac-sodium; compound 64 and bispyribac-sodium; compound 65 (and salts thereof) and bispyribac-sodium; compound 94 and bispyribac-sodium; compound 95 (and salts thereof) and bispyribac-sodium; compound 96 and bispyribac-sodium; compound 135 (and salts thereof) and bispyribac-sodium; compound 4 and clefoxidim; compound 9 and clefoxidim; compound 58 and clefoxidim; compound 64 and clefoxidim; compound 65 (and salts thereof) and clefoxidim; compound 94 and clefoxidim; compound 95 (and salts thereof) and clefoxidim; compound 96 and clefoxidim; compound 135 (and salts thereof) and clefoxidim; compound 4 and cinosulfuron; compound 9 and cinosulfuron; compound 58 and cinosulfuron; compound 64 and, cinosulfuron; compound 65 (and salts thereof) and cinosulfuron; compound 94 and cinosulfuron; compound 95 (and salts thereof) and cinosulfuron; compound 96 and cinosulfuron; compound 135 (and salts thereof) and cinosulfuron; , compound 4 and cyclosulfamuron; compound 9 and cyclosulfamuron; compound 58 and cyclosulfamuron; compound 64 and cyclosulfamuron; compound 65 (and salts thereof) and cyclosulfamuron; compound 94 and cyclosulfamuron; compound 95 (and salts thereof) and cyclosulfamuron; compound 96 and cyclosulfamuron; compound 135 (and salts thereof) and cyclosulfamuron; compound 4 and ethoxysulfuron; compound 9 and ethoxysulfuron; compound 58 and ethoxysulfuron; compound 64 and ethoxysulfuron; compound 65 (and salts thereof) and ethoxysulfuron; compound 94 and ethoxysulfuron; compound 95 (and salts thereof) and ethoxysulfuron; compound 96 and ethoxysulfuron; compound 135 (and salts thereof) and ethoxysulfuron; compound 4 and epoprodan; compound 9 and epoprodan; compound 58 and epoprodan; compound 64 and epoprodan; compound 65 (and salts thereof) and epoprodan; compound 94 and epoprodan; compound 95 (and salts thereof) and epoprodan; compound 96 and epoprodan; compound 135 (and salts thereof) and epoprodan; compound 4 and flucetosulfuron; compound 9 and flucetosulfuron; compound 58 and flucetosulfuron; compound 64 and flucetosulfuron; compound 65 (and salts thereof) and flucetosulfuron; compound 94 and flucetosulfuron; compound 95 (and salts thereof) and flucetosulfuron; compound 96 and flucetosulfuron; compound 135 (and salts thereof) and flucetosulfuron; compound 4 and imazosulfuron; compound 9 and imazosulfuron; compound 58 and imazosulfuron; compound 64 and imazosulfuron; compound 65 (and salts thereof) and imazosulfuron; compound 94 and imazosulfuron; compound 95 (and salts thereof) and imazosulfuron; compound 96 and imazosulfuron; compound 135 (and salts thereof) and imazosulfuron; compound 4 and metamifop; compound 9 and metamifop; compound 58 and metamifop; compound 64 and metamifop; compound 65 (and salts thereof) and metamifop; compound 94 and metamifop; compound 95 (and salts thereof) and metamifop; compound 96 and metamifop; compound 135 (and salts thereof) and metamifop; compound 4 and pyrazosulfuron-ethyl; compound 9 and pyrazosulfuron-ethyl; compound 58 and pyrazosulfuron-ethyl; compound 64 and pyrazosulfuron-ethyl; compound 65 (and salts thereof) and pyrazosulfuron-ethyl; compound 94 and pyrazole-ethyl; compound 95 (and salts thereof) and pyrazosulfuron-ethyl; compound 96 and pyrazosulfuron-ethyl; compound 135 (and salts thereof) and pyrazosulfuron-ethyl; compound 4 and guinclorac; compound 9 and guinclorac; compound 58 and guinclorac; compound 64 and guinclorac; compound 65 (and salts thereof) and guinclorac; compound 94 and guinclorac; compound 95 (and salts thereof) and guinclorac; compound 96 and guinclorac; compound 135 (and salts thereof) and guinclorac; compound 4 and flucarbazone-sodium; compound 9 and flucarbazone-sodium; compound 58 and flucarbazone-sodium; compound 64 and flucarbazone-sodium; compound 65 (and salts thereof) and flucarbazone-sodium; compound 94 and flucarbazone-sodium; compound 95 (and salts thereof) and flucarbazone-sodium; compound 96 and flucarbazone-sodium; compound 135 (and salts thereof) and flucarbazone-sodium; compound 4 and propoxycarbazone sodium; compound 9 and propoxycarbazone sodium; compound 58 and propoxycarbazone sodium; compound 64 and propoxycarbazone sodium; compound 65 (and salts thereof) and propoxycarbazone-sodium; compound 94 and propoxycarbazone sodium; compound 95 (and salts thereof) and propoxycarbazone-sodium; compound 96 and propoxycarbazone sodium; compound 135 (and salts thereof) and propoxycarbazone-sodium; compound 4 and amicarbazone, compound 9 and amicarbazone; compound 58 and amicarbazone; compound 64 and 'amicarbazone; compound 65 (and salts thereof) and amicarbazone; compound 94 and amicarbazone; compound 95 (and 'salts thereof) and amicarbazone; compound 96 and amicarbazone; compound 135 (and salts thereof) and amicarbazone; compound 4 and florasulam; compound 9 and florasulam; compound 58 and florasulam; compound '64 and florasulam; compound 65 (and salts thereof) and florasulam; compound 94 and florasulam; compound 95 (and salts thereof) and florasulam; compound 96 and florasulam; compound 135 (and salts thereof) and florasulam; compound 4 and triasulfuron; compound 9 and triasulfuron; compound 58 and triasulfuron; compound 64 and triasulfuron; compound 65 (and salts thereof) and triasulfan; compound 94 and triasulfuron; compound 95 (and salts thereof) and triasulfuron; compound 96 and triasulfan; compound 135 (and salts thereof) and triasulfuron; compound 4 and triaziflam; compound 9 and triaziflam; compound 58 and triaziflam; compound 64 and triaziflam; compound 65 (and salts thereof) and triaziflam; compound 94 and triaziflam; compound 95 (and salts thereof) and triaziflám; compound 96 and triaziflam; compound 135 (and salts thereof) and triaziflam; compound 4 and pinoxaden; compound 9 and pinoxaden; compound 58 and pinoxaden; compound 64 and pinoxaden; compound 65 (and salts thereof) and pinoxaden; compound 94 and pinoxaden; compound 95 (and salts thereof) and pinoxaden; compound 96 and pinoxaden; compound 135 (and salts thereof) and pinoxaden; compound 4 and tritosulfuron; compound 9 and tritosulfuron; compound 58 and tritosulfuron; compound 64 and tritosulfuron; compound 65 (and salts thereof) and tritosulfuron; compound 94 and tritosulfuron; compound 95 (and salts thereof) and tritosulfuron; compound 96 and tritosulfuron; compound 135 (and salts thereof) and tritosulfuron; compound 4 and amidosulfuron; compound 9 and amidosulfuron; compound 58 and amidosulfuron; compound 64 and amidosulfuron; compound 65 (and salts thereof) and amidosulfuron; compound 94 and amidosulfuron; compound 95 (and salts thereof) and amidosulfuron; compound 96 and amidosulfuron; compound 135 (and salts thereof) and amidosulfuron; compound 4 and metosulam; compound 9 and metosulam; compound 58 and metosulam; compound 64 and metosulam; compound 65 (and salts thereof) and metosulam; compound 94 and metosulam; compound 95 (and salts thereof) and metosulam; compound 96 and metosulam; compound 135 (and salts thereof) and metosulam; compound 4 and sulfosulfuron; compound 9 and sulfosulfuron; compound 58 and sulfosulfuron; compound 64 and sulfosulfuron; compound 65 (and salts thereof) and sulfosulfuron; compound 94 and sulfosulfuron; compound 95 (and salts thereof) and sulfosulfuron; compound 96 y, sulfosulfuron; compound 135 (and salts thereof) and sulfosulfuron; compound 4 and pyraflufen-ethyl; compound 9 and pyraflufen-ethyl; compound 58 and pyraflufen-ethyl; compound 64 and pyraflufen-ethyl; compound 65 (and salts thereof) and pyraflufen-ethyl; compound 94 and pyraflufen-ethyl; compound 95 (and salts thereof) and pyraflufen-ethyl; compound 96 and pyraflufen-ethyl; compound 135 (and salts thereof) and pyraflufen-ethyl; compound 4 and HOK-201; compound 9 and HOK-201; compound 58 and HOK-201; compound 64 and HOK-201; compound 65 (and salts thereof) and HOK-201; compound 94 and HOK-201; compound 95 (and salts thereof) and HOK 201; compound 96 and HOK-201; compound 135 (and salts thereof) and HOK-201; compound 4 and KUH-021; compound 9 and KÜH-021; compound 58 and KUH-021; compound 64 and KUH-021; compound 65 '(and salts thereof) and KUH-021; compound 94 and KUH-021; compound 95 (and salts thereof) and KUH-021; compound 96 and KUH-021; compound 135 (and salts thereof) and KUH? 021; compound 4 and CUH-35; compound 9 and CUH-35; compound 58 and CUH-35; compound 64 and CUH-35; compound 65 (and salts thereof) and CUH-35; compound 94 and CUH-35; compound 95 (and salts thereof) and CUH-35; compound 96 and CUH-35; compound 135 (and salts thereof) and CUH-35. The proportions of the compounds of the invention with other active herbicidal ingredients in herbicidal compositions are generally in the ratio of 100: 1 to 1: 100, most commonly 10: 1 to 1:10 and much more commonly 5: 1 at 1: 5 in weight. The optimum proportions can be easily determined by those skilled in the art on the basis of the desired weed elimination spectrum. It is particularly notorious because of a greater than additive (ie, synergistic) efficacy in certain weeds with the mixtures of compounds of the invention with auxin transport inhibitors (phytotropins) an example is the combination of the compound 1 (6-amino-5). ethyl-2-cyclopropyl-4-pyrimidinecarboxylate) with diflufenzopyr. The auxin transport inhibitors are guimic substances that inhibit the transport of auxin in plants, for example by binding with an auxin carrier protein. Other examples of auxin transport inhibitors include naptalam (also known as N- (1-naphthyl) phthalamic acid and 2 - [(1-naphthalenylamino) carbonyl] benzoic acid), 9-hydroxy-fluorene-9-carboxylic acid and 2-acid. 3, 5-triiodobenzoic acid. Therefore, one aspect of the present invention relates to a herbicidal mixture that compenεnds synergistically effective amounts of a compound of claim 1 and an auxin transport inhibitor. The synergistically effective amounts of auxin transport inhibitors with the compounds of the invention can be easily determined. The compounds of this invention can also be used in combination with herbicide sanitizers such as benoxacor, BCS (l-bromo-4- [(chloromethyl) sulfonyl] benzene), cloguintocet-mexyl, cymidorin, dichlormid, 2- (dichloromethyl) - 2-methyl-l, 3-dioxolane (MG 191), fenchlorazole-ethyl, phenchlorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpirethyl, methoxyphenone ((4-methoxy-3-methylphenyl) (3-methylphenyl) methanone) , naphthalic anhydride (1, 8-naphthalic anhydride) and oxabetrinyl to increase safety for certain crops. Effective amounts have been such that the herbicide sanitizers can be applied at the same time as the compounds of this invention or can be applied as a seed treatment. Therefore, one aspect of the present invention relates to a herbicidal mixture comprising a mixture of this invention and an antidotal effective amount of the herbicidal sanitizer. The seed treatment is particularly selective for the elimination of weeds, because it physically limits the antidoting of the harvest plants. Therefore, a particularly useful embodiment of the present invention is a method for eliminating selectively growing unwanted vegetation in a crop which comprises contacting the harvest site with an effective herbicidal amount of a compound of this invention wherein the seed from which the crop will grow is treated with an effective antidotal amount. of sanitizer. The antidotal effective amounts of sanitizers can be easily determined by a person skilled in the art by simple experimentation. The compounds of this invention can also be used in combination with plant growth regulators such as aviglycine., N- (phenylmethyl) -lii-purin-6-amine, e-ninoleone, gibberellic acid, gibberellin A and A7, harpina protein, mepicuat chloride, calcium prohexadione, prohydrojasmone, sodium nitrophenolate and trinexapac-methyl and modifying organisms growth of plants such as Bacillus cereus strain BP01. The following tests demonstrate the efficiency of elimination of the compounds of the invention against specific weeds. The control of weeds provided by the compounds, however, is not limited to these species. See index tables A-D for descriptions and compounds. The following abbreviations are used in the index tables which follow: t means tertiary, s means secondary, n means normal, i means iso, c means cycle, Me means methyl, Et means ethyl, Pr means propyl, i-Pr means isopropyl , Bu means butyl, Ph means phenyl, MeO means methoxy, EtO means ethoxy and CN means cyano. The symbol "T" means negative formal charge and the symbol "" means positive formal charge. The abbreviation "dec." It indicates that the budget seems to decompose when it melts. The abbreviation "Ex." indicates an "Example" and is followed by a number indicating in which example the compound is prepared.
INDEX TABLE A See index table D for H NMR data, TABLE B INDEX * See index table D for the NMR data - "" H INDEX TABLE C * See index table D for RMN data ^? INDEX TABLE D Compound 1H NMR data (CDC13 solution, unless otherwise indicated) 3 5 d 5.60 (broad s, 1H), 3.96 (s, 3H), 3.02 (d, 3H), 2.10 (m, 1H, 1.10 (m, 2H), 0.98- (m, 2H), 11 d 5.20 (broad s, 2H), 4.97 (s, 2H), 3.49 (s, 3H), 2.07 (m, 1H), 1.02 (m, 2H), 0.95 (, 2H), 12 d 5.20 (broad s, 2H), 4.18 (c, 2H), 3.80 (s, 2H), 1.90 (m, 1H), 1.25 (t, 3H), 1.01-0.93 (m, 4H) 13 d 5.26 (broad s, 2H), 3.82 (s, 2H), 3.73 (s, 3H), 1.90 (m, 1H), 1.02-0.92 (m, 4H) .19 d 8.60 ( s, 1H, 3.97 (s, 3H), 3.20 (s, 3H), 3.19 (s, 3H), 2.10 (m, 1H), 1.08 (m, 2H), 0.99 (m, 2H). 7.65 (s broad, 1H), 5.94 (s broad, 2H), 5.8 (s broad, 1H), 2.01 (m, 1H, 1.03 (m, 4H), 23 d 8.35 (m, 2H), 7.46 (m, 3H), 5.61 (broad s, 2H), 4.02 (s, 3H), 24 d 10.01 (s, 1H), 5.31 (s broad, 2H), 2.10 (m, 1H), 1.10-0.95 (m, 4H), 25 d 5.15 (s broad, 2H), 3.98 (s, 3H), 2.03 (m, 1H), 1.04-0.92 (m, 4H), 26 d 9.98 (s, 1H), 5.60 (s broad, 2H), 2.10 (m, 1H), 1.10-1.02 ( m, 4H). 27 d 8.19 (s, 1H), 1.89 (m, 1H), 0.92-0.87 (m, 4H). 30 d 5.12 (broad s, 2H), 4.45 (c, 2H), 2.13 (m, 1H), 1.41 (t, 3H), 1.04-0.92 (m, 4H). 31 d 5.66 (s, 1H), 5.34 (broad s, 2H), 4.30 (c, 2H), 1.98 (m, 1H), 1.30 (t, 3H), 1.13-0.92 (m, 4H). 32 d 5.26 (broad s, 2H), 4.21-4.07 (m, 3H), 1.94 (m, 1H), 1.45 (d, 2H), 1.22 (t, 3H), 1.09-0.90 (m, 4H). 33 d 8.57 (s, 1H), 4.18 (c, 2H), 3.88 (s, 2H), 3.18 (s, 3H), 3.16 (s, 3H), 2.00 (m, 1H), 1.24 (t, 3H) , 1.05-0.96 (m, 4H). 34 d 5.48 (broad s, 2H), 4.38 (c, 2H), 2.02 (, 1H, 1.36 (t, 3H), l.ll-0.97 (m, 4H). 35 d 3.97 (s, 3H) , 2.07 (m, 1H), 1.20-1.13 (m, 2H), 1.12-1.04 (m, 2H), 38 d 6.20 (s broad, 1H), 4.43 (c, 2H), 3.48 (m, 2H), 2.50 (m, 2H), 2.27 (s, 6H), 2.07 (m, 1H), 1.41 (t, 3H), 1.07 (m, 2H), 0.96 (m, 2H). 39 d 5.90 (broad s, 1H), 4.43 (c, 2H), 3.65 (m, 2H), 3.54 (m, 2H), 3.39 (s, 3H, 2.08 (m, 1H), 1.41 (t, 3H) , 1.04 (m, 2H), 0.98 (m, 2H), 40 d 8.59 (s, 1H), 4.44 (c, 2H), 3.20 (s, 3H), 3.18 (s, 3H), 2.10 (m, 1H), 1.41 (t, 3H), 1.11-1.05 (m, 2H), 1.01-0.94 (m, 2H) 41 d 8.27 (m, 2H), 7.39 (m, 2H) , 5.39 (broad s, 2H), 4.23 (c, 2H), 3.93 (s, 2H), 1.29 (t, 3H), 42 d 6.70 (s broad, 1H), 4.43 (c, 2H), 4.0 (s) broad, 2H), 2.10 (m, 1H), 1.41 (t, 3H), 1.11 (m, 2H), 1.01 (m, 2H). 43 d 8.35 (m, 2H), 7.10 (dd, 2H), 5.54 (broad s, 2H), 4.02 (s, 3H). 44 d 8.47 (d, 2H), 7.69 (d, 2H), 5.61 (broad s, 2H), 4.04 (s, 3H). 45 d 5.56 (s, 1H), 5.29 (broad s, 2H), 3.96-3.74 (m, 2H), 3.71-3.58 (m, 2H), 2.14-2.03 (m, 1H), 1.30-1.23 (m m, 6H), 1.07-0.89 (m, 4H). 46 d 5.39 (s, 1H), 4.96 (s broad, 2H), 3.49 (s, 6H), 15-2.04 (m, 1H), 1.02-0.87 (m, 4H). 47 d 6.32 (s, 1H, 5.34 (s broad, 2H), 4.28 (c, 2H), 2.21 (s, 3H), 2.03-1.93 (m, 1H), 1.28 (t, 3H), 1.10-0.91 ( m, 4h) .48 d 8.41 (s, 1H), 5.34 (broad s, 2H), 4.12 (s, 3H), 2.19-2.10 (m, 1H), 0.90-0.80 (m, 4H) 49 (DMSO -d6) d 8.45 (c, 1H), 7.34 (s, 1H), 6.82 (s broad), 2.86 (d, 3H), 1.91-1.81 (m, 1H), 1.07-0.92 (m, 4H). 50 d 7.23 (s, 1H), 5.19 (broad s, 2H), 3.21 (s, 6H), 2.19-2.08 (m, 1H), 1.05-0.88 (m, 4H). 51 (DMSO-de) d 11.68 + 11.55 (2 xs, 1H), 8.39 + 8.09 (2 xs, 1H), 2.20 + 1.97 (2 xs, 3H), 1.97-1.86 (m, 1H), 0.90 (d, 4H). 52 d 8.76 + 8.07 (2 xs, 1H), 4.50-4.32 (broad s, 2H), 3.94 + 389 (2 xs, 3H), 2.26-2.11 (broad m, 1H), 1.40 (broad s, 3H), 1.20-1.12 (m, 2H), 1.09-1.00 (m, 2H). 53 d 4.49 (c, 2H), 2.30 (s, 3H), 2.3-2.2 (m, 1H), 1.43 (t, 3H), 1.27-1.09 (m, 4H). 54 d 7.47-7.34 (m, 5H), 5.06 (s, 2H), 4.43 (c, 2H), 1.90-1.94 (m, 1H), 1.41 (t, 3H), 1.23-1.03 (m, 4H). 55 d 8.64 + 7.64 (2 x s, 1 H), 4.45 + 4.36 (2 x c, 2H), 2.20-2.10 (m, 1H), 1.42 + 1.37 (2 x t, 3H), 1.34 + 1.32 (2 x s, 9H), 1.18-0.98 (, 4H). 56 d 4.42 (c, 2H), 3.77 (m, 4H), 2.07-1.97 (m, 1H), 1.91 (m, 4H), 1.40 (t, 3H), 1.07-0.89 (m, 4H). 57 d 5.37-5.30 (m, 3H), 4.51 (d, 1H), 4.28-4.16 (m, 2H), 2.06-1.96 (m, 1H), 1.27 (t, 3H), 1.09-0.94 (m, 4H ). 59 d 5.14 (broad s, 2H), 3.97 (s, 3H), 3.84 (s, 3H), 2.09 (m, 1H), 1.00 (m, 2H), 0.94 (m, 2H). 60 d 8.46 (d, 2H), 7.69 (d, 2H), 5.65 (broad s, 2H), 4.50 (m, 2H), 1.46 (t, 3H). 61 d 8.23 (d, 2H), 7.24 (d, 2H), 5.57 + 5.53 (2 x s broad, 2H), 4.49 (m, 2H), 2.40 (s, 3H), 1.45 (t, 3H). 62 d 8.23 (d, 2H), 7.24 (d, 2H), 5.53 (s broad, 2H), 4.49 (m, 2H), 2.40 (s, 3H), 1.45 (t, 3H). 63 d 8.35 (m, 2H), 7.11 (t, 2H), 5.57 (broad s, 2H), 4.49 (m, 2H), 1.45 (t, 3H). 66 d 8.46 (d, 1H), 8.20 (dd, 1H), 7.50 (d, 1H), 5.62 (broad s, 2H), 4.50 (m, 2H), 1.46 (t, 3H). 67 d 7.67 (d, 1H), 7.48 (d, 1H), 7.32 (dd, 1H), 5.69 (broad s, 2H), 4.47 (m, 2H), 1.43 (t, 3H). 68 d 7.96 (dd, 1H), 7.83 (d, 1H), 6.85 (d, 1H), 6.02 (s, 2H), 5.53 (s broad, 2H), 4.48 (, 2H), 1.45 (t, 3H) . 69 d 8.97 (t, 1H), 7.23-7.15 (m, 2H), 5.67 (broad s, 2H), 4.48 (m, 2H), 1.44 (t, 3H). 70 d 8.11 (m, 1H), 8.06 (m, 1H), 7.19 (d, 1H), 5.57 (broad s, 2H), 4.49 (m, 2H), 2.32 (t, 3H), 2.30 (t, 3H) ), 1.45 (t, 3H). 71 d 8.11 (m, 1H), 8.06 (m, 1H), 7.20 (d ,. 1H), 5.50 (s broad, 2H), 4.49 (m, 2H), 2.33 (t, 3H), 2.31 ( t, 3H), 1.45 (t, 3H). 72 d 7.67 (d, 1H), 7.48 (d, 1H), 7.32 (dd, 1H), 5.63 (broad s, 2H), 4.48 (m, 2H), 1.43 (t, 3H). 73 d 9.46 (d, 1H), 8.20 (dd, 1H), 7.50 (d, 1H), 5.56 (s broad, 2H), 4.50 (m, 2H), 1.46 (t, 3H). 74 d 7.95 (dd, 1H), 7.83 (d, 1H), 6.86 (d, 1H), 6.02 (s, 2H), 5.48 (s broad, 2H), 4.48 (m, 2H), 1.45 (t, 3H). 79 d 5.56 (broad s, 1H), 3.97 (s, 3H), 3.04 (d, 3H), 2.11 (m, 1H), 1.10 (m, 2H), 0.98 (m, 2H). 81 d 7.82 (broad s, 1H), 5.48 (broad s, 2H), 2.97 (d, 3H), 2.01 (m, 1H), 1.04 (m, 2H), 0.99 (m, 2H). 82 d 8.22 (d, 2H), 7.24 (d, 2H), 5.57 + 5.52 (2 x s broad, 2H), 4.02 (s, 3H), 2.40 (s, 3H). 83 d 8.29 (d, 2H), 7.40 (d, 2H), 5.60 (broad s, 2H), 4.02 (s, 3H). 84 d 8.22 (d, 2H), 7.24 (d, 2H), 5.53 (s broad, 2H), 4.02 (s, 3H), 2.40 (s, 3H). 88 (DMSO-d5) d 14.1-13.9 (s broad), 8.25 (d, 2H), 7.56 (d, 2H). 89 (DMSO-de) d 8.15 (d, 2H), 7.29 (d, 2H), 2.36 (s, 3H). 90 (DMSO-d6) d 14.2-13.9 (broad s), 8.29 (m, 2H), 7.31 (t, 2H). 91 d 8.18 (d, 2H), 7.30 (d, 2H), 5.84 (broad s, 2H), 2.43 (s, 3H). 92 d 8.35 (m, 2H), 7.11 (t, 2H), 5.59 (broad s, 2H), 4. 02 (s, 3H). 93 d 8.32 (, 2H), 7.17 (t, 2H), 5.96 (broad s, 2H). 97 d 8.11 (, 2H), 7.31 (m, 2H), 5.57 (s broad, 2H), 4. 02 (s, 3H), 2.42 (s, 3H). 98 d 8.30 (d, 2H), 6.94 (d, 2H), 5.48 (broad s, 2H), 4. 49 (c, 2H), 3.86 (s, 3H), 1.45 (t, 3H). 99 d 8.24 (d, 2H), 7.26 (d, 2H), 5.51 (broad s, 2H), 4. 49 (c, 2H), 2.70 (c, 2H) 1.45 (t, 3H), 1.26 (t, 3H). 100 d 8.35 (s, 1H), 8.24 (d, 1H), 7.46-7.34 (t, 2H), 5.56 (s broad, 2H), 4.50 (c, 2H), 1.46 (t, 3H). 103 d 8.39 (d, 2H), 7.27 (d, 2H), 5.47 (broad s, 2H), 4. 50 (c, 2H), 1.45 (t, 3H). 114 d 8.19 (d, 2H), 7.38 (d, 2H), 5.26 (broad s, 2H), 4. 98 (s, 2H, 4.24 (c, 2H), 1.26 (t, 3H), 120 d 8.27 (d, 2H), 7.39 (d, 2H), 5.34 (broad s, 2H), 4.23 (c, 2H). , 3.91 (s, 2H), 1.29 (t, 3H), 124 d 8.61 + 8.48 (2 xs, 1H), 7.48 + 7.12 (2 xc, 1H), 3.98 + 3.96 (2 xs, 3H, 2.30-2.15 ( m, 1H), 2.14 + 2.00 (2 xd, 3H), 1.19-1.12 (2 xm, 2H), 1.06-0.97 (2 xm, 2H), 125 d 4.61 + 4.54 (2 xs wide, 2H), 4.47- 4.36 (m, 2H), 2.18-1.98 (broad m, 1H), 1.44-1.34 (m, 3H), 1.32-1.00 (broad m, 4H), 126 d 7.83 (d, 1H), 7.69 (d, 1H) ), 4.45 (c, 2H), 2.14 (s, 3H), 1.41 (t, 3H), 1.08-1.00 (, 4H), 127 d 8.89 (s, 1H), 8.43 (d, 1H), 7.97 (d, 1H), 7.92-7.83 (m, 2H), 7.57-7.46 (m, 2H), 5.57 (s broad, 2H), 4.53 (c, 2H), 1.48 (t, 3H), 138 d 8.11 ( d, 2H), 7.76 (d, 2H), 5.65 (s, 1H), 5.39 (s broad, 2H), 3.88 (, 2H), 3.70 (m, 2H), 1.30 (t, 6H), 140 d 5.38 (s broad, 2H), 4.44 (dd, 1H), 4.28 (dd, 1H), 3.35 (m, 1H), 2.88 (dd, 1H), 2.76 (dd, 1H), 2.07 (m, 1H), 1.05 (m, 2H), 1.00 (m, 2H). The 1H NMR data is n ppm downfield from tetramethylsilane. In this table the couplings are designated by (s) -singulete, (d) -double, (t) -triplete, (c) quartet, (m) multiplet, (dd) -doubled double, (dt) -double of triplets, (dc) -doubled quartet, (brs) 'broad singlet, (brd) -d broad, (brm) -multiplete wide.
BIOLOGICAL EXAMPLES OF THE INVENTION TEST A Weed seeds were planted (Echinochloa crus-galli), crabgrass (Digitaria sanguinalis), giant carrion (Setaria faberi), morning glory (Ipomoea spp.), Red-rooted ash (Amaranthus retroflexus) ) and alcotán (Abutilón theophrasti) in a mixture of soil of black earth and sand and it is treated, before the completion, with a directed spray in soil using test gum substances formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time these species are also treated with post-germination applications of test guanine substances formulated in the same way. Plants vary in height from 2 to 10 cm and are in the stage of 1 to 2 leaves for post-germination treatment. Treated plants and untreated controls are kept in a greenhouse for approximately 10 days, time after which all the treated plants are compared with the untreated controls and evaluated visually to determine the damage. The plant response classifications, summarized in Table A, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete elimination. A response with a hyphen (-) means that there are no test results.
Table A Compounds Table A Compounds 2000 g ai / ha 1 57 2000 g ai / ha 43 Post-germination Post-germination Weedy poultry 75 75 Poultry weeds 20 Garranchueló 80 30 Garranchuelo 30 Giant Carricera 75 85 Giant Carricera 10 Dondiego of day 100 80 Dondiego of day 45 Ashen 100 95 Ashen 85 Alcotán 85 80 Alcotán 50 Table A Compounds 500 g ai / ha of 120 57 58 59 60 61 62 63 64 65 66 67 68 Post-germination Weed stock 75 0 25 10 30 0 60 80 0 70 85 0 0 0 Garranchuelo 65 0 10 10 10 0 5 35 0 70 80 0 5 0 Giant barnyard 70 0 60 50 35 0 25 80 0 80 95 0 0 0 Morning glory day 95 40 70 80 100 20 30 35 25 95. 95 30 60 35 Ashen 100 60 75 80 80 40 50 60 65 100 100 65 90 55 Alcotán 95 55 50 85 85 40 100 95 70 100 100 75 75 60 Table A Compounds 500 g ai / ha of 6970 71 72 73 74 75 76 77 78 79 80 81 82 Post-germination Barnyard weeds 5 0 0 0 5 70 90 90 90 90 90 90 30 50 Garranchuelo 40 20 5 30 35 60 90 70 90 80 75 70 10 0 Giant barnyard 55 0 0 0 45 70 90 90 90 80 90 90 30 0 Morning glory 90 10 0 70 65 30 90 95 100 90 95 95 80 40 Ashen 90 20 30 95 80 70 100 95 95 95 100 95 75 75 Alcotán 90 60 55 85 75 80 100 100 100 90 95 90 75 90 Table A Compounds 500 g ai / ha of 83 84 85 86 87 88 89 90 91 92 93 94 95 96 Post-germination Barnyard weeds 10 80 0 30 90 85 85 10 90 0 0 60 90 25 Garranchuelo10 10 0 0 10 85 10 20 15 5 0 50 80 20 Giant bark 10 20 0 0 30 90 45 30 75 0 0 65 85 35 Morning glory 75 20 75 20 15 85 30 65 30 75 55 75 80 65 Ashen 85 65 90 50 90 95 100 90 100 70 70 85 95 85 Alcotán 90 90 60 85 95 95 95 85 95 70 80 90 95 85 Table A Compounds 500 g ai / ha 97 98 99 199 101 102 103 104 105 106 107 108 109 110 Post-germination Barnyard weeds 10 20 0 10 0 0 0 10 25 5 0 5 10 10 Garranchuelo 0 10 0 0 0 10 0 30 45 0 5 0 10 10 Giant barnyard 0 15 0 0 0 0 0 5 10 0 35 10 10 5 Morning glory 50 0 0 55 0 15 0 40 70 35 0 90 80 85 Ashen 30 15 10 25 5 65 20 45 90 70 10 85 85 85 Alcotán 70 45 35 70 15 70 70 80 95 55 65 65 80 65 Table A Compounds 500 g ai / ha 111 112 113 114 115 116 117 118 119 120 121 122 123 127 Post-germination Barnyard weeds 10 0 90 0 0 0 90 0 5 40 5 0 10 0 Garranchuelo 30 0 55 0 0 0 90 20 0 5 0 0 0 0 Carricera gigante 0 0 85 0 0 0 90 15 0 0 0 0 10 0 Morning glory day 50 50 90 55 60 60 90 70 35 55 10 0 20 0 Ashen 85 40 90 55 45 35 100 75 45 35 0 0 0 10 Alcotán 85 35 95 5 40 40 100 95 10 65 0 0 0 80 Table A Compounds 500 g ai / ha 128 129 130 131 132 133 134135 136 137138 139140 141 Post-germination Weeds 0 0 0 20 10 40 0 90 80 0 0 90 90 90 Garranchuelo 0 0 0 30 10 55 0 65 70 0 0 70 80 90 Giant barley 0 0 0 30 5 60 0 80 80 0 0 80 90 85 Morning glory 80 70 0 20 50 85 0 100 80 30 20 90 90 90 Ashen 75 85 15 70 65 90 30 95 100 45 35 100100100 Alcotán 80 90 30 60 60 85 55 100 95 60 70 90 90 100 Table A Compounds 500 g ai / ha 142 143 144 145 146 147148 149 150 Post-germination Weedy poultry 75 75 90 60 90 90 90 90 95 Crab tree 25 60 80 30 80 75 85 75 80 Giant barnyard 45 80 80 70 85 90 80 80 85 Morning glory 90 90 95 95 100 100100 95 100 Ash 90 90 100 90 95 95 95 90 90 Alcotán 90 95 100 95 100 100 95 100 100 Table A Compounds 500 g ai / ha 43 Table A Compounds 500 g ai / ha 128 129 130 131 132 133 134 135 136 137 138 139 140 141 Post-germination Poultry weeds 0 0 0 20 10 40 0 90 80 0 0 90 90 90 Garranchuelo 0 0 0 30 10 55 0 65 70 0 0 70 80 90 Giant bark 0 0 0 30 5 60 0 80 80 0 0 80 90 85 Day glory day 80 70 0 20 50 85 0 100 80 30 20 90 90 90 Ashen 75 85 15 70 65 90 30 95 100 45 35100100100 Alcotán. 80 90 30 60 60 85 55 100 95 60 70 90 90 100 Table A Compounds 500 g ai / ha 142 143 144 145 146 147148 149 150 • Post-germination Barnyard weeds 75 75 90 60 90 90 90 90 95 Crab tree 25 60 80 30 80 75 85 75 80 Giant barnyard 45 80 80 70 85 90 80 80 85 Morning glory 90 90 95 95 100 100100 95 100 Ash 90 90 100 90 95 95 95 90 90 Alcotán 90 95 100 95 100 100 95 100 100 Table A Compounds 500 g ai / ha 43 Post-germination Barnyard weeds 10 Garranchuelo 10 Giant barnyard 10 Dondiego of day 20 Ash 60 Alcotán 50 Table A Compounds 500 g ai / ha 20 58 59 60 61 62 63 64 65 66 67 68 69 70 Post-germination Poultry weeds 0 5 0 0 35 15 0 25 85 0 0 0 0 0 Garranchuelo 0 5 0 0 0 0 0 50 55 0 5 0 20 0 Giant barnyard 0 0 0 0 0 0 0 70 85 0 0 0 0 0 Morning glory day 50 55 90 0 10 10 20 80 75 20 50 15 75 0 Ashen 40 70 60 10 25 30 40 90 100 50 90 50 90 15 Alcotán 10 70 60 30 70 90 55 95 95 50 65 60 85 35 Table A Compounds 500 g ai / ha of 71 72 73 74 75 76 77 78 79 70 81 82 83 84 Post-germination Weeds, barnyard 0 0 0 30 85 90 90 80 85 55 0 40 0 55 Garranchuelo 0 10 15 30 80 45 70 70 40 30 0 0 0 0 Carricera - gigante 0 0 15 60 90 90 85 70 80 70 0 0 0 0 Dondiego by day 0 55 50 40 90 90 95 80 90 90 50 20 55 5 Ashen 5 95 75 60 90 85 90 85 90 65 55 45 70 60 Alcotán 40 85 70 70 85 80 95 75 90 65 50 90 90 75 Table A Compounds 500 g ai / h 85 86 87 88 89 90 91 92 93 94 95 96 9798 Post-germination Poultry weeds 0 10 50 50 60 0 75 0 0 30 75 20 30 0 Garranchuelo 0 0 0 60 0 0 5 0 0 35 70 5 0 0 Giant barley 0 0 0 80 10 0 5 0 0 45 85 25 0 0 Morning glory day 20 0 0 60 0 20 5 45 40 70 75 60 45 0 Ashen 75 20 55 90 50 35 55 35 45 80 85 70 10 5 Alcotán 25 90 90 90 70 65 75 45 65 90 90 80 60 35 Table A Compounds 500 g ai / ha 99 100 101 102 103 104 105 106 107 108 109 110 111 112 Post-germination Poultry weeds 0 0 0 0 0 0 10 0 0 0 0 0 0 0 Garranchuelo 0 0 0 10 0 15 20 0 0 0 0 0 5 0 Giant barnyard 0 0 0 .0 0 0 10 0 0 0 0 0 0 0 Dondiego by day 0 40 0 0 0 25 50 20 0 70 70 70 20 55 Ashen 5 10 0 50 0 30 65 15 10 50 60 55 55 20 Alcotán 0 50 0 45 45 70 85 25 35 35 25 40 75 20 Table A Compounds 500 g ai / ha 113 114 115 116 117 118 119 120 121 122 123 127 128 129 Post-germination Poultry weed 55 0 0 0 85 0 0 10 0 0 0 0 0 0 Garranchuelo 25 0 0 0 75 10 0 0 0 0 0 0 0 0 Carricera gigante 65 0 0 0 80 0 0 0 0 0 0 0 0 0 0 Morning glory day 90 40 35 40 90 65 40 25 0 0 0 0 55 60 Ashen 80 45 10 20 100 60 25 20 0 0 0 0 55 80 Alcotán 80 0 30 15 100 90 0 50 0 0 0 60 65 80 Table A Compounds 500 g ai / ha 130 131 132 133 134 135 136 137 138 139 140 141 142 143 Post-germination Poultry weeds 010 0 10 0 75 50 0 0 80 70 80 45 55 Garranchuelo 0 10 5 30 0 65 35 0 60 65 25 15 5 Giant barley 0 15 0 15 0 75 75 0 80 85 40 30 25 Morning glory day 0 0 45 70 0 90 70 5 0 80 85 90 90 90 Ashen 0 50 50 80 15 90 85 25 20 90 90 90 85 70 Alcotán 0 35 50 80 50 85 85 45 60 85 90 85 80 75 Table A Compounds 500 g ai / ha 144 145 146 147 148 149 150 Post-germination Barnyard weeds 60 30 70 80 68 65 80 Garranchuelo 40 5 20 25 10 25 65 Giant barnyard 70 20 80 60 45 60 80 Morning glory 85 80 85 85 90 80 80 Ash 85 80 90 85 75 75 90 Alcotán 95 75 85 80 75 85 90 Table A Compounds Table A Compounds 2000 g ai / ha 1 57 2000 g ai / ha 43 Post-germination Post-germination Poultry weed 80 80 Poultry weeds 10 Garranchuelo 75 70 Garranchuelo 10 Giant Carricera 85 70 Carricera Gigante 10 Dondiego of day 100 100 Dondiego of day 45 Ashen 100 100 Ashen 75 Alcotán 80 95 Alcotán 20 Table A Compounds 500 g ai / ha 1 20 57 58 59 60 61 62 63 64 65 66 6768 Post-germination Poultry weeds 60 0 25 0 15 0 10 45 40 60 90 0 0 0 Garxanchuelo25 0 10 0 0 0 30 60 75 90 90 15 30 0 Giant barnyard 40 0 10 10 0 0 10 0 35 70 80 0 30 0 Day glory 85 60 100 25 100 0 15 35 0 70 90 0 0 0 Ashen 85 70 90 60 70 0 30 75 80 100 100 10 75 15 Alcotán 60 70 80 40 45 0 50 75 15 95 95 35 40 10 Table A Compounds 500 g ai / ha of 6970 71 72 73 74 75 76 77 78 79 80 8182 Post-germination Barnyard weeds 15 0 0 0 30 50 95 90 10075 80 80 20 15 Garranchuelo 75 20 0 0 35 50 90 75 80 70 80 85 10 0 Giant bark 50 5 0 0 15 40 90 85 95 65 95 70 10 0 Morning glory 0 0 0 0 0 30 100 100 100100100 100 50 0 Ash 85 10 15 100 60 40 95 90 95 90 100 90 70 70 Alcotán - 65 35 50 55 40 50 95"100 10085 90 90 40 35 Table A Compounds 500 g ai / ha 83 84 85 86 87 88 89 90 9192 93 94 9596 Post-germination Poultry weeds 5 25 0 0. 20 55 50 35 80 0 30 40 80 10 Garranchuelo 5 15 5 0 75 85 60 50 75 0 45 55 85 65 Giant barley 0 20 0 0 0 50 10 15 25 0 35 40 90 10 Morning glory day 10 0 20 0 20 90 0 25 50 0 5 35 85 80 Ashen 50 80 60 5 100 100 100 80 100 45 90 95 100 80 Hobby 30 70 10 10 95 70 75 45 100 45 85 90 95 80 Table A Compounds 500 g ai / ha 97 98 99 199 101 102 103 104 105 106107108109 110 Post-germination Poultry weeds 0 0 0 0 0 0 0 5 0 5 0 15 2515 Garranchuelo 25 15 0 0 0 0 0 10 0 0 5 20 2515 Giant barnyard 5 0 0 0 0 0 0 5 0 0 0 0 5 0 Dondiego by day 0 0 0 0 0 0 0 0 0 0 0 90 9590 Ashen 70 0 0 0 0 15 10 10 0 30 0 75 80 65 Alcotán 50 5 0 0 0 20 10 10 0 30 10 50 50 35 Table A Compounds 500 g ai / ha 111 112 113 114 115 116 117 118 119 120 121 122 123 127 Post-germination Barnyard weeds 0 10 80 0 20 20 85 10 10 15 0 0 0 0 Garranchuelo 0 10 70 0 10 10 75 25 0 0 0 0 0 0 Giant barnyard 0 0 80 0 0 0 85 15 0 0 0 0 0 0 Morning glory 0 10 100 0 35 50 85 0 0 0 0 0 0 0 Ashen 0 30 90 0 40 50 100 55 0 0 0 0 0 0 Alcotán 0 10 95 0 10 15 100 15 0 0 0 0 0 0 Table A Compounds 500 g ai / ha 128 129 130 131 132 133 134135 136137138 139 140141 Post-germination Poultry weeds 0 0 0 0 0 15 0 90 40 0 0 90 90 70 Garranchuelo 0 0 0 0 0 45 0 95 60 0 0 90 90 85 Giant bark 0 0 0 0 0 30 0 85 60 0 0 90 85 85 of day 0 0 0 0 0 35 0 100 20 0 0 100 95 95 Ashen 0 15 0 0 65 65 0 100 100 0 0 100 95 85 Alcotán 0 5 0 0 5 30 0 100 75 0 0 90 95 85 Table A Compounds 500 g ai / ha "142 143 144 145 146 147 148 149 150 Post-germination Weedy poultry 75 85 80 75 90 85 85 85 80 Crab 85 95 95 80 75 80 90 75 80 Giant barnyard 65 75 80 60 90 85 80 90 80 Morning glory 95 100 95 100 100 100 100 100 100 Ash 90 95 85 85 95 90 90 90 95 Alcotán 85 95 85 85 100 95 100 85 95 Table A Compounds 500 g ai / ha of 43 Post-germination Barnyard weeds 0 Garranchuelo 0 Giant barnyard 0 Dondiego of day 0 Ash 0 Alcotán 0 Table A Compounds 500 g ai / ha 20 58 59 60 61 62 63 64 65 66 67 68 69 70 Post-germination Barnyard weeds 0 0 0 0 0 0 0 0 50 0 0 0 0 0 Garranchuelo 0 0 0 0 0 0 0 25 60 0 0 0 50 5 Giant Carricera 0 0 0 0 0 0 0 15 40 0 0 0 10 5 Day glory 10 10 80 0 0 0 0 45 25 0 0 0 0 0 Ashen 40 0 20 0 0 0 0 20 100 0 10 0 65 0 Alcotán 0 0 10 0 0 0 0 25 55 0 10 5 35 20 Table A Compounds 500 g ai / ha 71 72 73 74 75 76 77 78 79 70 81 82 83 84 Post-germination Poultry weeds 0 0 5 0 70 75 90 45 30 10 10 0 0 0 Garranchuelo 0 0 5 20 85 30 70 55 30 45 0 0 0 0 Giant barnacle 0 0 0 0 75 70 75 10 40 15 0 0 0 0 Morning glory 0 0 0 0 95 100 100 90 55 90 0 0 0 0 Ashen 0 75 15 0 90 80 85 75 90 80 60 0 20 0 Alcotán 30 40 35 30 80 90 100 80 60 75 20 5 1515 Table A Compounds 500 g ai / h 85 86 87 88 89 90 91 92 93 94 95 96 97 98 Post-germination Poultry weeds 0 0 0 10 0 0 5 0 5 5 20. 5 0 0 Garranchuelo 0 0 10 35 0 10 25 0 25 45 65 50 15 0 Giant barnyard 0 0 0 10 0 0 0 0 5 20 65 5 5 0 Dondiego by day 0 0 0 10. 0 0 5 0 0 30 80 15 0 0 Ashen 50 0 85 80 80 70 100 15 80 90 95 80 25 0 Alcotán 0 0 25 10 20 10 80 10 55 75 55 65 45 0 Table A Compounds 500 g ai / ha 99 100 101 102 103 104 105 106107108 109 110 111 112 Post-germination Poultry weeds 0 5 0 0 0 0 0 0 0 10 0 0 0 0 Garranchuelo 0 10 0 0 0 0 0 0 0 0 0 0 0 0 Giant barnyard 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Morning glory 0 0 0 0 0 0 0 0 0 0 30 0 0 0 Ash 0 20 0 10 0 0 0 0 0 55 50 40 0 10 Alcotán 0 0 0 10 0 0 0 5 0 10 15 25 0 0 Table A Compounds 500 g ai / ha 113 114 115 116 117 118 119 120 121122 123 127 128129 Post-germination Poultry weeds 25 0 0 10 25 0 0 5 0 0 0 0 0 0 Garranchuelo 15 '0 0 0 45 10 0 0 0 0 0 0 0 0 Carricera gigante 15 0 0 0 50 0 0 .0 0 0 0 0 0 0 Morning glory 90 0 25 30 10 0 0 0 0 0 0 0 0 0 Ashen 80 0 30 30 65 20 0 0 0 0 0 0 0 0 Alcotán 65 0 5 0 55 0 0 0 0 0 0 0 0 0 Table A Compounds 500 g ai / ha 130 131 132 133 134 135 136 137138 139140 141142 143 Post-germination Poultry weeds 0 0 0 0 0 65 5 0 0 75 70 35 50 65 Garranchuelo 0 0 0 0 0 75 20 0 0 75 70 60 45 70 Giant barnyard 0 0 0 0 0 30 10 0 0 80 40 5 25 35 Morning glory day 0 0 0 0 0 95 10 0 0 90 90 85 85 90 Ashen 0 0 15 10 0 85 45 0 0 90 90 80 70 65 Alcotán 0 0 0 10 0 80 30 0 0 90 90 80 85 90 Table A Compounds 500 g ai / ha of 144 145146 147 148 149 150 Post-germination Barnyard weeds 65 30 65 70 65 70 65 Garranchuelo 75 65 35 70 45 20 50 Carricera giant 35 0 60 40 40 35 50 Morning glory 80 75 95 95 90 85 90 Ash 75 65 75 80 80 70 70 Alcotán 75 70 85 75 80 70 75 TEST B Seeds are selected from poultry weeds (Echinochloa crus-galli), Surinam (Brachiaria decumbens), Ajonjera (Xanthium strumarium), Corn (Zea mays), Crabgrass (Digi taria sanguinalis), Giant carrion grass (Setaria faberii), chenopodium (Chenopodium album), day morning glory (Ipomoea coccinea), ash (Amaranthus retro flexus), alcotán (Abutilon theophrasti) and wheat (Triticum aestivum) and are treated before germination with test chemicals which are formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, selected plants of these crop and weed species and also alopecuro (Alopecurus myosuroides) and wild oats (Avena fatua) are treated with post-germination applications of the test chemicals formulated in the same way. The plants vary in height from 2 to 8 cm (stage of 1 to 4 leaves) for post-germination treatments. The plant species in the flooded paddy trial consist of rice (Oryza sativa), African sedge _ (Cyperus difformis), duckweed (Heteranthera limosa) and barnyard weed (Echinochloa crus-galli) that grow until the 2nd stage. sheets for test. The treated plants and controls are kept in a greenhouse for 13 to 15 days, after which all species are compared to the controls and evaluated visually. The plant response classifications, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete elimination. A hyphen (-) in the answer means that there is no result in the test.
Table B Compounds 1000 g ai / ha 1 2 3 4- 5 7 8 9 1011 12 13 1415 flooded land Poultry weeds 80 90 0 90 50 20 70 90 0 0 0 0 8090 Duckweed 80 90 0 100 90 0 90 100 0 70 20 0 8080 Rice 70 60 0 80 0 0 60 80 0 0 20 0 2070 African sedge 20 90 0 80. 90 0 40 90 0 20 0 0 5070 Table B "Compounds 1000 g ai / ha 16 17 18 19 21 22 23 24 25 26 27 28 3031 flooded land Poultry weeds 90 80 0 80 60 80 0 0 30 60 0 0 0 30 Duckweed 90 90"80 80 80 90 30 0 40 90 60 30 0 60 Rice 70 50 0 60 40 60 0 10 30 70 20 0 0 20 African sedge 60 50 70 50 0 20 40 80 60 0 0 Table B Compounds 1000 g ai / ha 32 33 34 35 36 37 38 39 40 41 42 44 4546 flooded land Poultry weeds 0 0 0 0 0 20 0 0 70 0 0 0 0 0 Duckweed 0 0 0 0 0 100 0 0 80 90 0 90 0 60 Rice 0 0 0 0 0 0 0 0 60 0 0 0 0 0 African sedge 0 0 0 0 0 90 0 0 70 80 0 80 0 30 Table B Compounds 1000 g ai / ha 47 48 49 50 51 124 flooded land Poultry weeds 0 20 50 30 0 0 Duckweed 80 20 60 40 0 0 Rice 0 0 30 30 0 0 African sedge 70 0 70 0 0 Table B Compounds 500 g ai / ha 58 59 60 64 75 76 77 78 79 80 83 88 9192 flooded land Poultry weeds 0 0 20 0 70 70 60 40 0 50 0 0 20 0 Duckweed 100 0 90 100 70 70 80 70 70 70 100 90 100 90 Rice 0 0 0 0 70 50 50 40 20 50 0 0 0 0 African sedge 100 0 30 90 10 70 40 50 0 70 100 90 9090 Table B Compounds 500 g ai / ha 94 95 96 113 117 128 129 133 135 136 flooded land Poultry weeds 0 30 10 0 70 30 20 0 80 20 Duckweed 100 100 100 0 100 100 100 90 90 90 Rice 0 40 0 0 50 0 0 0 60 40 African sedge 90 90 90- 0 90 100 100 90 80 90 Table B Compounds 250 g ai / ha 64 flooded land. farmyard 0 Lentil of water 100 Rice 0 African sedge 70 Table B Compounds 125 g ai / ha 58 59 60 64 75 76 77 78 79 80 83 88 91 92 flooded land Poultry weeds 0 0 0 0 0 0 Lens of water 100 0 80 90 0 0 40 20 10 50 100 90 10080 Rice 0 0 0 0 0 0 20 0 0 0 African sedge 90 0 0 0 0 30 0 10 0 20 90 60 8080 Table B Compounds 125 g ai / ha 94 95 96 113 117 128 129 133 135 136 flooded land Poultry weeds 0 0 0 0 20 0 0 0 30 0 Duckweed 100 90 100 0 100 90 100 90 60 90 Rice 0 0 0 0 20 0 0 0 20 0 African sedge90 90 90 0 80 90 90 90 70 90 Table B Compounds 62 g ai / ha 64 flooded land Poultry weeds 0 Lentil de agua 80 Rice 0 African sedge 0 Table B Compounds 500 g ai / ha 23 5 7 8 9 10 11 12 13 14 15 16 17 Post-germination Barnyard weeds 90 10 90 30 90 90 10 90 40 10 90 90 90 90 Alopecuro 80 50 80 80 0 80 0 60 0 20 60 80 70 70 Mange 100 100 100 100 100 100 70 90 70 40 70 100 100100 Corn 80 0 90 30 90 90 0 0 0 0 70 80 80 80 Garranchuelo90 40 90 30 90 90 40 70 30 30 30 60 80 50 Giant barnyard 80 40 50 40 90 90 10 50 30 20 50 70 80 70 Chenopodium 100 100 100 100 100 100 90 10080 70 100 100 100100 Morning glory 100 100 100 90 100 100 80-10080 70 100 100 100 100 Wild oat 70 30 60 70 0 70 10 10 0 0 70 70 60 50 Ashen 100 90 100 90 100 100 90 90 80 70 90 100 100 90 Surinam grass 90 30 80 20 90 90 10 50 0 0 50 90 90 80 Alcotán 100 80 90 90 100 100 80 80 60 50 70 90 90 100 Wheat 70 20 60 80 0 70 0 40 0 0 50 70 60 60 Table B Compounds 500 g ai / ha 18 19 21 22 23 24 25 26 27 28"30 31 32 33 Post-germination Poultry weeds 0 90 0 90 0 10 80 60 0 50 80 0 70 20 Alopecuro 0 80 20 80 10 10 60 70 30 30 70 0 40 40 Ajonjera 70 100 10 100 90 70 90 90100100 100 80 90 80 Corn 0 70 0 80 0 10 30 20 20 0 30 0 10 0 Garranchuelo 0 80 0 90 0 40 80 70 10 50 90 30 20 20 Giant barnyard 0 80 0 80 10 30 80 40 30 40 90 0 20- 40 Chenopodium 90 100 20 100 80 80 90 80 90 90 100 70 80 70 Morning glory 70 100 30 100 70 90 90 80 90 90 100 70 90 70 Wild oat O 70 O '60 10 O 20 40 30 10 70 O 30 20 Ashen 70 100 30 100 70 80 100 80 70 90 100 50- 80 80 Suriname pasture 0 90 0 90 10 10 70 60 0 50 80 0 10 0 Alcotán 50 100 30 100 70 50 70 70 70 90 90 60 50 50 Wheat 0 60 20 70 20 0 30 30 30 10 60 0 30 20 Table B Compounds 500 g ai / ha 34 35 36 37 38 39 40 41 42 44 46 47 48 49 Post-germination Barnyard weeds 60 90 0 90 0 70 90 70 30 50 30 60 20 70 Alopecuro 70 70 40 60 0 0 60 60 60 40 10 0 20 50 Ajonjera 80 100 70 100 0 50 90 - 90100 0 100 80 100 Corn 0 60 0 70 0 50 60 80 0 70 0 0 0 30 Garranchuelo30 50 0 80 20 40 80 20 30 80 30 60 20 80 Giant bark 50 60 10 60 0 30 60 30 0 - 10 50 10 70 Chenopodium 90 100 50 100 60 90 100 90 90 90 30 90 80 90 Morning glory day 70 100 70 100 40 100 100 90 90100 90 90 80 100 Wild Oats 40 60 40 0 0 0 60 0 0 0 0 0 20 60 Ash 80 100 30 100 30 70 100 90 90 90 80 80 80 90 Suriname pasture 50 80 0 70 20 30 70 10 10 50 10 20 10 60 Alcotán 60"90 40 100 50 ~ 70 90 70 80 90 0 40 60 80 Wheat 40 60 40 60 0 0 60 40 50 30 0 0 - 20 40"Table B Compounds 500 g ai / ha 50 51 52 54 55 56 124 125 126 Post-germination Barnyard weeds 50 60 80 70 50 30 40 70 0 Alopecuro 50 30 50 40 40 20 40 20 0 Ajonjera 90 90 60 80 80 20 80 60 0 Maize 40 0 60 20 20 0 0 0 10 Garranchuelo 80 60 60 30 30 0 40 30 20 Giant barnyard 70 30 60 30 20 0 20 40 0 Quenopodium 90 90 90 90 90 30 90 70 40 Morning glory 90 90 90 90 90 50 100 90 60 Wild oats 60 30 20 40 20 20 30 20 20 Ash 90 90 90 90 80 70 90 60 30 Surinam grass 60 40 30 0 0 0 0 10 70 Alcotán 90 80 50 60 30 0 50 50 20 Wheat 60 40 20 20 0 0 30 0 0 Table B Compounds Table B Compounds 250 g ai / ha 1 4 45 53 250 g ai / ha of 1 4 4553 Post-germination Post-germination Poultry weed 90 90 0 90 Morning glory 100 100 6090 Alopecuro 70 90 0 60 Wild Oats 60 80 0 60 Ajonjera 90 100 10 90 Ash 100 100 50100 Corn 70 90 0 70 Surinam grass 90 90 0 50 Garranchuelo 90 90 20 30 Alcotán 90- 100 20 80 Giant barnyard 80 90 0 70 Wheat 70 80 0 60 Chenopodium 100 100 30"100 Table B Compounds 125 g ai / ha 23 5 7 8 9 10 11 12 13 14 15 16 17 Post-germination Weeds 90 0 50 0 90 90 0 20 0 0 30 90 70 20 Alopecuro 50 20 70 60 0 60 0 20 0 10 30 70 10 0 Ajonjera 100 70 80 90 100 100 60 80 40 10 50 100 90 100 Corn 20 0 30 0 70 70 0 0 0 0 30 50 30 0 Garranchuelo 90 30 50 10 80 90 30 30 10 20 10 30 30 20 Giant barnyard 70 20 40 20 80 90 0 10 0 10 20 40 30 10 Chenopodium 100 100 100 80 100 90 80 90 60 60 100 100 100 100 Morning glory 100 80 100 80 100 100 80 80 60 50 100 100 100 100 Wild oats 40 10 40 40 0 20 0 0 0 0 20 10 10 0 Ash 100 80 90 0 100 100 80 80 50 50 80 80 90 70 Surinam grass 9 10 50 0 80 90 10 20 0 0 10 60 60 30 Alcotán 50 50 70 50 80 100 50 60 20 40 50 80 80 60 Wheat 40 10 50 50 0 40 0 0 0 0 20 40 30 0 Table B Compounds 125 g ai / ha 18 19 21 22 23 24 25 26 27 28 30 32 33 34 Post-germination Poultry weeds 0 80 0 70 0 0 40 20 0 20 0 20 0 0 Alopecuro 0 60 10 60 0 0 10 40 30 10 60 30 40 60 Ajonjera 70 90 0 100 30 50 90 80 100 90 100 40 60 80 Corn 0 30 0 20 0 0 0 0 0 0 0 0 0 0 Garranchuelo 0 40 0 50 0 20 60 40 10 30 30 10 10 0 Giant barnyard 0 20 0 70 0 20 50 30 20 20 0 10 10 20 Chenopodium 70 100 10 100 70 70 90 70 80 90 90 70 60 70 Morning glory 20 100 10 90 40 60 90 70 70 90 90 40 40 60 Wild oats 0 40 0 10 10 0 10 30 20 0 60 20 20 30 Ashen 20 90 0 100 30 70 90 70 60 80 90 80 60 50 Surinam grass 0 40 0 80 0 0 50 30 0 10 10 0 0 10 Alcotán 20 70 10 100 40 40 60 40 60 70 50 10 40 30 Wheat 0 20 10 0 0 0 20 30 20 0 50 20 20 30 Table B Compounds 125 g ai / ha 35 36 37 38 39 40 41 42 44 46 47 48 49 50_ Post-germination Weed stock 40 0 0 0 0 0 20 10 40 0 20 10 30 10 Alopecuro 60 0 40 0 0 50 20 30 30 0 0 0 20 30 Ajonjera 30 20 100 0 30 0 70 80 90 0 90 20 90 90 Corn 0 0 0 0 0 0 20 0 30 0 0 0 0 0 Garranchuelo 20 0 60 0 0 0 10 0 70 10 10 10 30 40 Giant barnyard 10 0 10 0 0 0. 20 0 - 0 10 10 10 20 Chenopodium 90 40 100 20 70 0 80 80 90 10 80 60 80 80 Morning glory day 70 10 90 10 80 0 70 80 80 80 80 30 90 90 Wild Oats 60 0 0 0 0 40 0 0 0 0 0 0 30 30 Ashen 70 20 100 30 50 0 70 80 80 70 70 60 90 80 Suriname pasture 20 0 20 0 0 - 0 0 0 - 0 0 0 10 20 Alcotán 50 20 80 0 40 0 50 50 80 0 20 10 50 70 Wheat 20 0 0 0 0 50 30 50 '0 0 0 0 30 30 Table B Compounds 125 g ai / ha 51 52 54 55 56 75 76 77 78 79 83 88 92 94 Post-germination Barnyard weeds 20 30 0 0 0 90 90 90 90 80 80 90 10 90 Alopecuro 20 0 40 30 0 60 60 60 40 50 60 60 20 60 Ajonjera 80 40 20 20 0 100 90 10010060 100 100 80 100 Corn 0 0 0 0 0 70 70 80 80 60 10 80 0 90 Garranchuelo30 0 20 0 0 80 90 80 70 60 60 80 .20 80 Giant barnyard 0 40 20 20 0 80 80 80 70 70 50 70 30 60 Chenopodium 80 80 80 70 20 100 100100100100 100 100 90 90 Morning glory day 80 90 80 80 0 100 100 100 100 100 100 90 60 90 Wild oats 20 0 '0 0 0 60 60 60 70 40 40 50 0 30 Ash 80 60 80 70 50 90 100100100100 100 100 80 90 Suriname grass 0 0 0 0 0 80 80 80 80 60 60 80 10 80 Alcotán 70 40 50 10 0 100 90 90 80 80 90 100 60 100 Wheat 30 0 0 0 0 70 70 60 7040 30 60 0 - 60 Table B Compounds 125 g ai / ha 95 113 117 124 125 126 128 129 133 135 136 Post-germination Poultry weeds 90 80 90 '0 0 0 60 70 70 90 90 Alopecuro - 40 70 0 0 0 50 70 70 70 70 Ajonjera 90 90 100 30 40 0. 90 100 100 100 100 Corn 90 40 90 0 0 0 70 80 80 80 70 Garranchuelo 80 40 80 10 20 0 40 70 70 70 80 Giant bark 80 50"80 10 0 0 50 50 70 80 70 Chenopodium 100 90 100 40 60 30 90 100 100 100 100 Morning glory 100 90 100 50 70 30 90 100 100 100 100 Wild Oats 60 50 50 0 0 0 40 40 60 60 50 Ash 100 90 100 50 60 0 90 100 100 100 100 Surinam grass 90 80 70 0 0 0 40 70 70 80 80 Alcotán 100 80 100 20 0 10 80 90 100 100 90 Wheat 50 50 70 0 0 0 20 20 50 60 60 Table B Compounds 62 g ai / ha 1 4 31 45 53 65 75 76 77 78 79 83 88 92 Post-germination Barnyard weeds 50 70 0 0 80 70 80 90 60 80 50 50 90 10 Alopecuro 40 70 0 0 20 70 50 50 50 20 20 50 40 20 Ajonjera 90 90 70 0 50 100 70 60 70 100 - 90 100 60 Corn 30 50 0 0 0 80 60 50 30 40 20 10 70 0 Garranchuelo 70 80 0 0 0 80 70 70 70 60 30 50 70 0 Giant barnyard 50 80 0 0 30 70 60 60 70 60 40 40 60 20 Chenopodium 100 100 40 10 90 100 90 100100 100 90 100100 90 Morning glory 90 90 50 40 90 80 100 100 100 100 90 60 60 50 Wild oats 20 50 0 0 30 40 50 50 50 50 30 0 40 0 Ash 90 100 20 30 80 100 80 90 90 80 80 100100 70 Surinam grass 60 90 0 0 10 80 70 70 70 60 20 50 80 0 Alcotán 90 70 10 0 40 90 70 90 80 70 50 80 90 50 Wheat 30 40 0 0 30 50 50 60 50 50 0 0 50 0 Table B Compounds 62 g ai / ha 94 95 113 117 128 129 133 135 136 Post-germination Barnyard weeds 80 90 50 90 40 60 70 70 70 Alopecuro 40 60 30 60 40 70 60 60 70 Ajonjera 100 90 90 100 70 70 100 100 90 Corn 70 80 10 90 10 70 70 50 40 Garranchuelo 70 80 20 60 20 50 60 60 70 Giant barnyard 50 80 20 80 30 40 60 80 60 Chenopodium - 90 100 80 90 90 100 100 100 100 Morning glory day 80 90 90 80 40 50 70 100 40 Wild Oats 30"30 40 30 0 0 40 60 20 Ash 90 100 70 100 90 100 90 100 90 Suriname pasture 80 80 30 70 30 50 60 80 70 Alcotán 90 100 60 > , 90 50 80 90 100 80 Wheat 40 40 30 50 0 0 0 40 20 Table B Compounds 4 g ai / ha 65 Post-germination Barnyard weed 20 Alopecuro 20 Ajonjera 80 Maíz 10 Garranchuelo 20 Table B Compounds 4 g ai / ha of 65 Post-germination Giant barnyard 40 Quenopodio 80 Dondiego of day 70 Wild oat 0 Ash 70 Table B Compounds 4 g ai / ha of 65 Post-germination Suriname pasture 20 Alcotán 50 Wheat 0 Table B Compounds 500 g ai / ha 2 3 5 7 8 9 10 11 12 13 14 15 16 17 Pre-germination Barnyard weeds 90 0 30 30 90 90 50 10 80 80 80 90 90 80 Ajonjera 100 80 80 80 100 100 90 90 90 100 80 100 100 90 Corn 80 0 70 0 90 80 0 0 30 30 70 80 70 60 Garranchuelo 90 50 70 30 90 100 60 80 70 70 80 90 100100 Giant barnyard 90 0 10 0 90 80 20 70 50 40 80 80 80 70 Chenopodium 100 90 100 90 100 100 90 100100 100 100 100 100 100 Morning glory 100 60 80 80 100 100 90 90 90 100 100100 100100 Ash 100 90 90 90 100 100 90 90 90 90 90 100 90 100 Surinam grass 90 20 10 0 90 90 0 70 - - 80 90 80 90 Alcotán 100 70 90 80 100 100 90 90 90 90 80 100 100 90 Wheat 70 50 30 80 80 0 50 60 60 50 60 60 60 Table B Compounds 500 g ai / ha 18 19 21 22 - 23 24 25 26 27 28 30 31 32 33 Pre-germination Weeds 0 90 10 20 0 20 60 90 60 30 40 70 10 50 Aj onj era 40 100 80 80 10 90 90 90 90 90 100 100 90 90 Corn 0 90 - - 0 0 0 80 50 - 0 80 40 0 30 Garranchuelo 0 90 60 100 0 80 70 90 70 80 90 80 40 50 _ Giant barnyard 0 80 10 20 0 60 80 80 40 50 80 80 0 40 Chenopodium 60 100 80 100 30 90 90 100 100 100 90 100 90 100 Morning glory 0 100 90 100 10 90 90 100 90 90 100 100 80 90 Ash 70 100 70 80 20 90 90 100 100 90 90 100 90 90 Suriname grass 0 90 20 20 0 50 70 80 70 60 80 60 0 40 Alcotán 40 100 80 100 20 80 8010090 90 80 90 80 80 Wheat 0 60 30 50 0 70 60 60 50 40 60 70 10 50 Table B Compounds 500 g ai / ha 34 35 36 37 38 39 40 41 42 44 46 47 48 49 Pregermination Weedy stock 0 80 0 40 0 20 90 10 0 10 0 40 10 60 Ajonjera 60 90 60 80 0 30 100 10 70 80 40 90 20 90 Maize 0 50 0 10 10 50 50 O 0 0 O 30 0 40 Garranchuelo 7O 80 0 90 0 50 80 20 20 80 40 90 - 90 Giant rabbit 20 70 0 60 0 20 80 0 40 50 40 50 70 Quenopodio 80 100 40 100 90 100 100 60 90 60 60 100 100100 Morning glory 70 100 0 50 50 70 10020 80 40 90 100 30 100 Ash 80 -100 20 100 70 100 100 60 90 80 90 90 80 100 Suriname grass 50 60 0 40 0 0 70 0 20 60 40 20 60 60 Alcotán 60 90 40 80 0 30 90 30 70 80 20 90 0 90 Wheat 10 50 0 60 0 10 70 20 10 60 20 50 30 70 Table B Compounds 500 g ai / ha 50 51 52 54 55 56 124 125 126 Pre-germination Weedy stock 50 0 30 40 60 0 0 - 0 Ajonjera 90 20 60 90 90 30 60 90 90 Maize 20 0 0 0 0 0 0 0 0 Garranchuelo 80 0 0 0 60 0 0 100 100 Giant barnyard 40 0 0 0 0 0 0 0 0 0 Quenopodio 100 80 - - - - 70 Morning glory 90 40 100 - 100 20 60 100 70 Ash 90 70 50 100 100 80 70 90 80 Pasture of Suriname 70 0 0 0 50 0 0 0 20 Alcotán. 90 30 80 90 30 50 90 20 Wheat 40 70 Table B Compounds 250 g ai / ha 1 4 45 53 Pregermination Stock weed 90 90 0 70 Ajonj era 100 100 0 100 Maize 80 80 - 0 Garranchuelo 90 90 0 50 Giant barnyard 90 80 0 50 Chenopodium 100 100 30 - Table B Compounds 250 g ai / ha of 1 4 45 53 Pre-germination Morning glory 100 100 50 100 Ash 100 100 50 100 Surinam grass 80 90 0 30 Alcotán 100 90 0 90 Wheat 60 70 0 40 Table B Compounds 125 g ai / ha 23 5 7 8 9 10 11 12 13 14 15 16 17 Post-germination Barnyard weeds 700 10 0 70 50 20 0 50 40 10 40 30 20 Ajonjera 90 80 70 70 90 90 80 80 80 90 60 70 70 80 Corn - 0 0 0 0 90 50 0 0 0 - 0 20 30 0 Garranchuelo90 10 20 0 80 90 20 30 20 50 10 70 70 70 Giant carrion 30 0 0 0 50 70 0 10 20 20 30 40 30 20 Chenopodium 100 70 90 -80 90 90 - 10090 90 90 90 100 90 Morning glory 100 50 70 70 100 100 80 80 70 90 70"70 90100 Ash 90 80 90 90 100 90 80 80 80 80 80 90 90 80 Suriname grass 40 0 0 .0 60 70 0 10 0 0 40 30 40 30 Alcotán 90 40 70 50 80 90 80 80 80 80 60 70 80 70 Wheat 60 0 - 0 60 40 0 0 30 40 40 40 50 40 Table B Compounds 125 g ai / ha 18 19 21 22 23 24 25 26 27 28 30 32 33 34 Post-germination Barnyard weeds 0 40 0 0 0 0 20 50 30 10 10 0 20 0 Egret 10 90 30 50 0 80 80 80 80 80 60 80 80 30 Corn 0 70 0 10 0 - 0 30 10 0 10 0 10 0 Garranchuelo 0 80 0 20 0 60 60 30 30 70 50 0 0 0 Giant barnacle 0 20 0 0 0 10 40 10 0 30 10 0 0 0 Quenopodio 10 100 70 70 0 70 90 10090 80 80 40 90 50 Morning glory 0 90 50 100 0 50 80 90 80 80 90 40 0 20 Ash 0 90 50 60 0 80 80 90 90 80 50 40 80 40 Suriname grass 0 60 0 0 0 10 20 10 0 - 0 0 0 10 Alcotán 0 90 10 30 0 50 70 90 80 80 10 50 70 30 Wheat 0 50 0 10 0 30 50 30 10 10 30 0 0 0 Table B Compounds 125 g ai / ha 35 3637 38 39 40 41 42 44 46 47 48 49 50 Post-germination Barnyard weeds 10 0 10 0 0 50 0 0 0 0 0 0 30 30 Aj onj era 60 10 20 0 10 90 0 40 10 0 80 0 80 80 Maize 0 0 0 0 30 0 0 0 0 0 0 0 10 20 Garranchuelo 30 0 50 0 0 60 0 0 40 0 20 10 80 50 Giant barley 0 0 10 0 0 20 0 0 20 0 20 30 40 10 Chenopodium 90 0 100 20 50 100 30 40 - 10 90 70 90 90 Morning glory 70 0 10 0 30 90 0 20 10 50 80 0 80 80 Ashen 80 0 100 10 70 90 0 50 70 80 80 60 90 70 Surinam grass 10 0 - 0 0 50 - 0 40 0 0 30 40 20 Alcotán 70 10 40 0 0 90 10 10 30 0 60 0 80 80 Wheat 20 0 30 0 0 40 0 10. 30 0 20 30 20 Table B Compounds 125 g ai / ha 51"5254 55 56 75 76 77 78 79 83 88 92 94 Post-germination Weed stock 80 90 90 70 70 30 - 30 - Aj onj era 0 10 50 70 0 90 100 100 100 80 50 90 50 50 Corn 0 - 0 0 0 80 80 80 70 60 0 10 0 0 Garranchuelo 0 0 0 50 90 90 90 90 70 50 70 10 70 Giant Carricera 0 0 0 0 90 80 90 70 20 10 30 10 20 Quenopodium - - - - 100 100 100 100 90 90 - 80 - Morning glory 0 10 0 80 100 100 100 100 90 10 10 0 0 Ashen 10 - 100 80 100 100 100 100100 100 80 - Suriname pasture 0 0 0 0 80 90 90 90 0 10 50 0 30 Alcotán 0 0 10 50 100 90 10090 80 60 90 70 70 Wheat 0 0 0 0 70 70 70 70 60 50 70 30 60 Table B Compounds 125 g ai / ha 95 113 117 124 125 126 128 129 133 135 136 Post-germination Poultry weed - 20 30 0 0 0 10 30 30 90 80 Manger 100 80 90 10 30 0 10 30 50 100 70 Corn 80 20 10 0 0 0 0 0 0 80 0 Garranchuelo 100 70 90 0 0 80 0 30 70 90 80 Giant barnacle 90 10 90 0 0 0 0 20 20 50 50 Chenopodium - 80 100 0 - 50 80 70 100 100 Morning glory day 60 60 20 10 30 0 0 0 0 100 40 Ashen - 90 100 20 30 20 50 90. 80 100 100 Surinam pasture 100 60 100 0 0 0 0 10 10 90 50 Alcotán 100 90 90 20 10 10 40 60 60 100 80 Wheat 80 60 80 0 0 0 0 20 60 90 70 Table B Compounds 62 g ai / ha 1 4 31 45 53 65 75 76 77 78 79 83 88 92 Post-germination Barnyard weeds 60 30 20 0 0 40 60 40 70 60 0 20 - 10 Ajonjera 90 80 90 - 60 80 90 80 80 80 50 10 60 40 Corn 20 0 0 0 0 0 50 70 70 30 30 0 0 0 Garranchuelo90 70 10 0 0 70 80 80 80 80 0 30 50 0 Giant barnyard 30 10 10 0 0 30 30 40 70 20 0 0 10 0 Chenopodium 100 90 90 0 - 90 100 9010090 90 70 - 50 Morning glory 90 60 90 30 90 30 80 10010080 70 0 0 0 Ash 90 90 90 0 60 100 100100100100 80 80 - 40 Suriname grass 50 40 20 0 0 40 70 70 60 60 0 0 20 0 Alcotán 90 80 80 0 20 70 80 80 80 70 50 50 70 50 Wheat 30 50 40 0 0 80 30 30 70 30 0 20 50 0 Table B Compounds 62 g ai / ha 94 95 113 117 128 129 133 135 136 Post-germination Barnyard weeds - - 0 10 0 10 30 70 30 Manger 30 90 70 50 0 10 20 100 40 Maize 0 40 0 0 0 - 0 50 0 Garranchuelo 40 80 40 90 0 10 40 80 70 Giant rabbit 0 50 0 20 0 0 0 60 10 Quenopodio - 70 90 10 - - 100 90 Morning glory 0 30 50 10 0 0 0 100 10 Ashen - - 70 100 10 80 70 100 80 Surinam grass 10 50 20 80 0 0 0 80 10 Alcotán 40 80 80 70 0 50 50 90 60 Wheat 30 70 10 50 0 0 50 70 50 Table B Compounds 4 g ai / ha of 65 Pre-germination Poultry weed 0 Ajonj it was 10 Corn 0 Garranchuelo 20 Table B Compounds 4 g ai / ha of 65 Pregermination Giant barnyard 0 Quenopodio 30 Dondiego of day 0 Ashen; 20 Table B Compounds 4 g ai / ha of. 65 Post-germination Surinam pasture 0 Alcotán 0 Wheat 0 TEST C Seeds or nuts of plant species that are selected from bermudagrass (Cynodon dactylon), surinamgrass (Brachiaria decumbens), winterjack (Xanthium strumarium), maize (Zea mays ), crabgrass (Digitaria sanguinalis), villous button grass (Eriochloa villosa), giant carrion (Setaria faberii), cuajaleche (Eleusine indica), Aleppo sorghum (Sorghum halepense), kochia (Kochia scoparia), chenopodium (Chenopodium album), morning glory (Ipomoea coccinea), oriental black sole (Solanum ptycanthum), yellow tiger nut (Cyperus esculentus), ash (Amaranthus retroflexus), common ragweed (Ambrosia elatior), soybean (Glycine max), common sunflower (oilseed) (Helianthus annuus), hobby (Abutilon theophrasti) is planted treated before germination with test chemicals that are formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, the selected plants of these crop weed species also of winter barley (Hordeum vulgare), alopecuro (Alopecurus myosuroides), birdseed (Phalaris minor), stelaria (Stellaria media), velvety bromeliad (Bromus tectorum), green fox tail (Setaria viridis), green grass (Lolium multiflorum), wheat (Tri ticum aestivum), wild oats (Avena fatua) wind grass (Apera spica-venti) are treated with applications subsequent to the germination of some the test chemicals formulated in the same way. The plants are classified in height from 2 to 18 cm (stage of 1 to 4 leaves), for later treatments of the germination. The plant species in a flooded paddy trial consist of rice (Oryza sativa), African sedge (Cyperus difformis), duckweed (Heteranthera limosa) barnyard weed (Echinochloa crus-galli) that grow to the 2-leaf stage for test. The treated plants controls are kept in a greenhouse for 12 to 14 days, after which all species are compared to the controls " are evaluated visually. The response ratings of the plants, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect 100 is complete elimination. A hyphen (-) in the answer means that there is no result in the test.
Table C Compounds 500 g ai / ha 1 2 4 5 9 14 15 1617 19 22 2637 flooded lPoultry weeds 25 75 85 20 85 45 75 50 50 60 70 0 0 Duckweed 0 95 100 0 90 55 85 85 80 60 95 40 100 Rice 0 65 80 0 75 0 50 65 75 20 60 25 0 African sedge 0 25 75 0 85 30 25 55 25 50 95 20 95 Table C Compounds 250 g ai / ha 1 2 4 5 9 14 15 16 17 19 22 26 37 flooded lPoultry weed 15 45 65 0 55 0 25 15 0 0 40 0 0 Duckweed 0 90 90 0 80 45 50 75 80 60 90 40 100 Rice 0 45 75 0 55 0 20 0 45 10 40 20 0 African sedge 0 0 65 0 15 0 10 50 20 50 75 20 90 Table C Compounds 125 g ai / ha 1 2 4 9 14 15 16 17 19 22 26 37 flooded lPoultry weeds 0 20 60 0 15 0 0 0 0 0 0 0 0 Duckweed - 70 80 0 70 40 45 65 0 40 60 40 95 Rice 0 25 40 0 30 0 0 0 0 0 20 0 0 African sedge - 0 30 0 15 0 0 - 0"0 50 30 0 85 Table C Compounds 62 g ai / ha 1 2 9 14 15 16 17 19 22 26 37"flooded land Poultry weeds 0 0 0 0 0 0 0 0 0 0 0 0 0 Duckweed 0 50 70 0 45 0 45 65 0 20 30 40 95 Rice 0 0 0 0 0 0 0 0 0 0 20 0 0 African sedge 0 0 0 0 0 0 0 _ 0 20 0 0 85 Table C Compounds 500 g ai / hal 4 5 8 10 15 22 27 28 35 37 49 50 post-germination Barley - 65 45 - 40 - Bermuda bermuda 9080 80 75 0 75 60 30 0 20 65 95 Alopecuro - 70 65 60 - Closed velvet - 70 40 - 30 -Alpiste 60 55 - 40 -Estelaria - 100 - 100 70 85 90 0 20 - 0 45 20 Ajonjera 100 100 100 30 100 75 100 100 25100 _ 95 95 90 Maize 45 95 45 0 90 0 75 65 0 0 - 25 25 65 Garranchuelo 90 80 80 25 75 0 80 85 30 20 - 60 95 80 Fluffy button grass 90 95 70 20 85 0 75 65 0 0 - 45 65 30 Giant barnyard 90 95 60 10 75 0 70 60 0 15 - 45 0 20 Carricera verde - 75 - - - - - - - - 65 - 60 - Cuajaleche 70 75 50 0 60 0 55 25 0 15 - 0 25 0 Aleppo sorghum 70 95 45 0 85 0 80 100 0 0 55 70 60 Kochia 100 100 100 80 100 100 100 100 60 95 - 95 10095 Chenopodium 100 100 100 80 100 100 100 95 50 95 - 95 95 85 Morning glory 100 100 100 65 100 95 100 100 85 95 - 95 10095 Yellow tigergrass 5 0 0 0 0 0 0 0 0 0 - 20 0 0 Wild Oats - 70 - - - - - - - - 55 - 60 - Enlargement 100 100 100 55 100 95 100 100 80 75 - 100 95 95 Ambrosia 100 100 100 75 100 90 95 90 50 95 - 95 90 80 Italian pasture - 65 - - - - - - - - 40 - 50 - Soy 100 100 100 60 100 100 100 100 95 95 - 100100 100 Suriname grass 95 95 70 0 80 0 65 85 0 0 - 0 45 60 Alcotán 100 100 95 40 95 90 90 95 30 75 - 95 80 80 Wheat - 65 - - - - - - - - 45 - 60 - Wind - 75 - - - - - - - - 65 - 60 - Table C Compounds 500 g ai / ha post-germination 51 Gram bermuda .0 Stelaria 45 Ajonjera 85 Maiz 0 Garranchuelo 45 Gooseberry grass 0 Table C Compounds 500 g ai / ha post-germination 51 Giant chanterelles 0 Chesnose 0 Aleppo sorghum 0 Kochia 95 Chenopodium 90 Morning glory 100 Table C Compounds 500 g ai / ha post-germination 51 Yellow tiger 0 Ashen 85 Ambrosia 85 Soya 95 Surinam pasture 0 Alcotán 65 Table C Compounds 250 g ai / ha 12 3 4 5 7 8 9 1015 16 17 22 27 post-germination Barley - 60 30 65 - - - - - - - - - - Bermuda grass 90 80 45 70 70 0 65 80 0 65 75 0 60 0 Alopecuro - 75 0 70 - - - - - - - - - -Bromeliad - 60 20 65 - - - - - - - - - - Alpiste - 40 10 60 - - - - - - - - - - Estelaria 90 95 40 100 20 0 95 100 20 65 35 85 85 0 Eggsman 100 85 90 100 100 30 100 100 60100 100 100 10025 Maize 40 30 0 90 40 0 70 95 0 55 55 20 60 0 Garranchuelo 85 70 0 75 70 5 70 80 0 65 75 65 85 5 Leafy button grass 90 75 0 85 50 0 75 85 0 65 65 20 60 0 Giant bark 80 70 0 85 50 0 70 80 0 65 65 35 50 0 Green barnyard - 70 35 70 - - - - - - - - - - Litter bin 40 45 0 65 40 0 45 45 0 40 20 0 20 0 Aleppo Sorghum 70 60"0 95 45 0 - 45 85 0 70 70 60 80 0 Kochia 100 100 100 100 100 70 100100 95 100 100 100 10050 Chenopodium 100 100 100 100 100 70 100100 90 100 100 100 95 25 Morning glory 100 100 75 100 100 55 100100 95 100 100 100 95 85 Yellow Tigernut 5 20 0 0 0 0 0 - 0 0 0 0 0 0 0 Wild Oats - 60 40 70 - - - - - - - - - - Ash 100 100 80 100 90 40 100100 95 85 95 95 10030 Ambrosia 100 95 95 100 95 65 95 100 80 90 95 95 90 40 Italian pasture - 60 35 65 - - - - - - - - - - Soy 100 100 95 100 100 35 100100 90 95 100 100 10085 Surinam grass 90 70 0 75 30 0 70 80 0 55 55 0 85 0 Alcotán 100 100 7 100 90 35 85 9580 85 90 95 90 0 Wheat - 65 10 65 - - - - - - - - - - Wind Grass - 70 30 70 - - - - - - - - - - Table C Compounds 250 g ai / ha 28 30 34 35 37 42 49 50 51 64 78 88 post-germination - Barley - - 40 40 - - 30 - - 100 90 - Bermuda grass 0 5 - - 0 5 55 90 0 70 65 80 Alopecuro - - 45 60 - - 50 - - 50 50 - Bromelia atercipelada - - 35 40 - - 0 - - 20 55 - Alpiste - - 45 45 - - 30 - - 10 0 Estelaria 15 85 - - 0 10 40 - 0 55 70 100 Ajonjera 95 100 - - 95 20 95 65 70 - 100 90 Corn 0 50 - - 15 0 20 60 0 - 40 30 Garranchue1o 0 50 - - 40 0 75 75 0 90 90 85 Fluffy button grass 0 40 - - 0 5 60 15 0 - 90 85 Giant bark 0 40 - - 40 0 0 0 0 50 70 85 Carricera verde - - 45 60 - - 50 - - 45 -75 - Cuajaleche 0 0 - - 0 0 20 0 0 70 50 80 Aleppo Sorghum 0 40 - - - 10 35 - 0 85 40 85 Kochia 95 100 - - 95 85 95 65 85 90 95 95 Chenopodium 85 90 - - 95 25 95 80 85 90 100100 Dondiego of day 95 95 - - 80 85 80 85 85 90 100 85 Yellow tiger nut - 5 - - 0 0 0 0 50 0 75 Wild Oats - - 50 45 - - 40 - - 10 60 - Ash 60 90 _ _ 100 30 95 85 80 100 100100 Ambrosia 90 90 - - 90 40 7545 80 90 100100 Italian pasture - - 60 40 - - 50 - 45 25 Soya 95 95 - 95 70 95100 95 100 100 100 Suriname pasture 0 35 - - 0 0 40 0 0 - 90 .85 Alcotán 70 60 - - 90 20 7570 60 95 100 95 Wheat - 35 45 - 50 - - 10 55 - Grass of the wind - - 60 65 - - 60 - - 60 40 - Table C Compounds 125 g ai / hal 2 3 4 5 7 8 9 10 11 15 16 17 19 post-germination Barley - 60 0 65 - - - - - - - - - 45 Gram bermuda 90 70 0 65 50 0 60 70 0 0 45 60 0 45 Alopecuro - 70 0 65 - - - - - - - - - 65 Bromelia atercipelada - 45 20 60 - - - - - - 60 Alpiste - 40 10 45 - - - - - - 65 Estelaria - 75 0 85 10 0 75 100 0 0 50 20 55 5 Ajonjera 100 85 75 100 95 30 100 100 15 40 100 10010090 Corn 15 20 0 80 40 0 20 65 0 0 15 20 0 35 Garranchuelo 85 60 0 75 50 0 65 75 0 20 45 45 20 70 Leafy button grass 80 70 0 70 50 0 60 70 0 0 50 0 0 65 Giant barnyard 65 65 0 75 30 0 60 75 0 0 60 55 0 55 Carricera verde 65 35 70 - - - - 60 Cuajaleche 0 0 0 20 5 0 0 40 0 0 0 0 0 0 Aleppo sorghum 30 25 0 80 40 0 35 80 0 0 55 60 40 - Kochia 100 95 90 100 100 65 100 100 90 90 95 10010090 Quenopodium 100 100 90 100 100 60 100 100 80 80 100 10010095 Morning glory 100 100 65 100 95 50 95 100 85 0 95 10010085 Yellow tigernut 0 0 0 0 0 0 0 0. 0 0 0 0 0 0 Wild oatmeal - 55 40 65 - - - - - - 65 Ashen 100 95 75 100 90 40 75 100 80 90 70 95 75 65 Ambrosia 100 90 80 100 95 35 80 95 65 75 85 95 95 80 Italian pasture - 60 35 60 - - - - - - 70 Soya 100 100 90 100 100 25 95 100 80 95 95 10010075 Surinam grass 90 65 0 75 20 0 65 75 0 0 20 25 0 - Alcotán 90 80 55 100 90 10 70 80 70 75 70 65 80 60 Wheat - 65 0 60 - - - - - - - - - 45 Wind grass - 70 30 65 - - - - "" - - - - - 60 Table C Compounds 125 g ai / ha 22 25 27 28 30 34 35 37 42 47 49 50 5164 post-germination Barley - - - - - 30 35 - - - 20 - - - Gra bermuda 60 0 0 0 5 - - 0 0 15 55 75 0 65 Alopecuro - - - - - 35 50 - - - 40 - - 50 Bromelia atercipelada - - - - - 30 30 - - - 0 - - 20 Alpiste - - - 35 45 - - - 20 - - 10 Estelaria 60 85 0 0 65 - - 0 0 0 0 0 0 0 Ajonjera 90 90 25 9 355 1 10000 - - 95 5 65 95 40 65100 Corn 40 0 0 0 0 - - 10 0 0 0 0 0 50 Garranchuelo 55 50 0 0 5 _ _ 15 0 20 65 60 0 85 Leafy button grass 60 30 0 0 0 - - 0 0 0 15 0 0 65 Giant bark 45 30 0 0 0 - - 0 0 0 0 0 0 50 Carricera verde - - - - - 45 50 - - - 20 - - 40 Cuajaleche 10 0 0 0 0 - - 0 0 0 0 0 0 60 Aleppo Sorghum 80 20 0 0 10 20 0 20 - 85 Kochia 100 85 20 85 100 90 50 100 45 55 60 90 Chenopodium 95 90 20 75"80 95 20 80 90 75 75 90 Morning glory 90 90 85 95 95 65 80 65 70 80 80 90 Yellow tigergrass 0 0 0 0 0 0 0 0 0 50 Avena silvestre - - - - - 45 45 - - - 40 - - 10 Ashen 100 100 20 35 80 - 95 20 70 80 80 70100 Ambrosia 85 70 20 80 85 - - 80 40 80 65 45 80 85 Italian pasture 45 40 30 - 35 Soya 100 90 45 85 90 85 40 75 95 95 95100 Surinam grass 60 0 0 0 20 0 0 0 60 Alcotán 60 45 50 60 - 85 0 0 70 55 2090 Wheat 30 40 - - 40 - - 10 Wind grass 50 55 - - 40 - 55 Table C Compounds 125 g ai / ha 65-76 78 79 83 88 94 117 129 133 135 136 post-germination Barley 50 - 30 35 - - - 45 - - 55 Gram bermuda 70 75 60 - 55 70 80 90 - 85 75 85 Alopecuro 65 5 60 - - - - 50 - - 65 Parental Bromeliad 55 - 15 35 - - - - 0 - - 55 Alpiste 45 0 35 - - - - 30 - - 65 Estelaria 70 95 - 30 100 95 - - 45 85 50 Mange 100 100 100 100 90 100 90 - 95 100 100 Corn 90 70 40 60 - 60 - - 80 35 75 Garranchuelo 90 90 90 75 80 85 90 _ 80 75 75 Fluffy button grass 85 95 - 60 85 90 85 - 70 80 70 Giant barnacle 70 85 65 - 40 80 80 80 - 75 75 85 Carricera verde 70 - 70 60 - - - - 60 - - 70 Cuajaleche 70 50 40 - 45 75 80 80 - 70 55 80 Aleppo Sorghum 85 95 20 - 70 75 90 50 - 95 70 95 Kochia 90 100 95 - 90 95 100 90 - 85 95 90 Chenopodium 95 100 95 - 100 95 100 95 - 100 95 95 Morning glory 95 100 100 - 90 85 100 50 - 100 95 100 Yellow tigerwort 50 60 0 - 75 55 75 60 - 80 40 75 Wild oats 40 - 60 45 - - - - 40 - 60 Ash 100 100 95 - 100 100 100 95 - 100 100 100 Ambrosia 95 100 95 - 95 100 100 100 - 95 95 95 Italian Pasture 60 - 20 45 - - - - 60 - 65 Soy 100 100 100 - 100 100 100 100 - 100 100 100 Surinam grass 80 - 55 - 65 80 100 80 - 70 60 70 Alcotán 90"95 95 - 100 95 95 95 - 95 95 95 Wheat 45 - - 30 40 - - - - 35 - 55 Grass of the wind 70 - 30 50 - - - - 60 - - 65 Table C Compounds 62 g ai / ha 1 2 3 4 5 7 8 9 10 11 15 16 1719 post-germination barley - 35 0 30 - - - - - - - - - 35 Gram Bermuda 70 60 0 40 5 0 50 65 0 0 0 0 0 30 Alopecuro - 65 0 65 - - - - - - - _ _ 65 Bromelia atercipelada - 35 20 45 - - - - - - - - - 50 Alpiste 40 10 35 - - - - - - - 60 Estelaria 80 65 0 30 0 0 20 85 0 0 20 0 0 5 Ajonjera 90 75 65 85 80 30 80 85 0 25 85 95 10050 Maize 10 15 0 0 10 0 0 55 0 0 15 0 0 0 Garranchuelo 30 55 0 70 4400 0 60 70 0 0 15 15 0 70 Leafy button grass 65 60 0 60 5 0 30 60 0 0 0 0 0 65 Giant barnyard 40 35 0 60 20 0 40 65 0 0 45 20 0 40 Carricera verde - 55 '30 65 - - - - - - - - - 45 Cuajaleche 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Aleppo Sorghum 30 0 0 70 0 0 30 65 0 0 20 0 0 0 Kochia 100 95 65 100 100 40 95 100 80 75 95 100 10090 Chenopodium 100 100 90 100 95 50 75 95 60 70 100 100 10090 Morning glory 100 75 60 15 95 - 95 95 70 0 90 95 95 80 Yellow tigernut 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wild Oatmeal - 55 30 60 - - - - - - - - 60 Ashen 90 80 65 100 85 20 70 70 65 80 65 90 6565 Ambrosia 100 85 75 100 90 25 60 80 45 65 75 85 8570 Italian pasture 45 35 45 - - - - - - - - 65 Soya 100 100 75 100 95 25 95 100 70 80 95 95 9575 Suriname pasture 90 55 0 60 0 0 _40 65 0 0 0 0, 0 45 Alcotán 85 70 55 80 55 0 60 75 65 60 65 60 5050 Wheat - 60 0 50 - - - - - - - - - 40 Wind Grass - 65 30 60 - - _ "_ _ _ _ _ - 60 Table C Compounds 62 g ai / ha 22 25 27 28 30 34 35 37 42 47 49 50 5164 post-germination Barley - - - - 20 20 - - - 0 - - 20 Grama Berrpuda 50 0 0 0 0 -. - 0 0 0 0 50 0 60 Alopecuro - - - - 35 50 - - - 40 - - 45 Bromelia atercipelada - - - - - 0 30 - - - 0 - - 15 Alpiste - - - - 30 35 - - - 0 - - 5 Estelaria 30 40 0 0 50 - - 0 0 0 0 0 0 0 Ajonjera 90 90 20 85 95 - - 0 0 60 75 40 65 90 Corn 30 0 0 0 0 - - 0 0 0 0 0 0 50 Garranchuelo 50 30 0 0 0 _ - 0 0 0 0 60 0 80 Pastilla de fluffy button 60 0 0 0 0 - - 0 0 0 0 0 0 40 Giant bark 40 5 0 0 0 - - 0 0 0 0 0 0 20 Carricera verde - - - - - 40 40 - - - 0 - - 30 Cuajaleche 10 0 0 O Y - - 0 0 O O O O 35 Sorghum of alepo 40 10 0 0 5 - - 0 0. 0 - 0 0 80 Kochia 95 85 0 75 90 - - 0 30 20 20 20 15 85 Chenopodium 90 85 20 60 60 - - 0 20 70 70 '70 60 90 Morning glory 90 90 20 80 90 - - 0 50 40 50 65 80 90 Yellow tigernut 0 0 0 0 0 - - 0 0 0 0 0 0 50 Avena silvestre - - - - - 40 30 - 30 - - 5 Ashen 85 80 5 30 70 - - 0 10 45 65 75 65 95 Ambrosia 80 65 5 65 80 - - 0 10 40 45 20 65 80 Italian Pasture - - - - - 40 40 - 30 - - 30 Soy 95 90 30 75 90 - - 20 30 65 95 95 75 90 Suriname pasture 55 0 0 0 0 - - 0 0 0 0 0 0 60 Alcotán 55 45 0 45 10 - - 0 0 0 45 50 0 85 Wheat - - - - - 20 35 - 20 - - 0 Wind grass - _ _ _ _ 40 40 40 - 55 Table C Compounds 62 g ai / ha 65 76 78 79"83 88 94 95 117 129 133 135136 post-germination Barley 50 - 5 35 - - - - - - 45- - 50 Gram Bermuda 70 75 60 - 20 70 75 85 85 - 85 60 80 Alopecuro 65 - 5 60 - - - - - 50 - - 65 Bromelia atercipelada 50 - 10 30 - - - - - 0 - 45 Alpiste 35 - 0 25 - - - - - 30 - - 55 Estelaria 60 70 0 - 10 100 50 95 40 - 20 25 50 Mangera 100100 100 - 70 90 90 100 90 - 95 - 100 Corn 90 55 40 - 50 0 35 35 - - 60 20 55 Crabgrass 90 85 90 - 65 80 85 80 90 - 75 75 75 Downy button grass 85 80 55 - 45 75 90 80 80 - 60 60 70 Giant barnyard 70 55 30 - 20 75 80 80 70 - 70 65 75 Carricera verde 60 - 40 30 - - - - - 40 - 70 Cuajaleche 70 45 0 - 30 75 80 80 75 - 65 45 75 Aleppo Sorghum 85 - 10 - 55 45 75 90 50 - 90 65 85 Kochia 85 95 90 - 75 95 95 95 90 - 85 90 90 Chenopodium 90 100 95 - 95 95 95 100 95 - 95 90 95 Morning glory 90 95 90 - 90 - 90 95 50 - 100 95 90 Chufa a marilla 20 40 0 - 60 45 70 75 50 - 75 15 75 Wild Oats 20 - 10 25 - - - - - 40 - - 55 'Ash 100"100 80 - 100 100 100 100 95 - 95 100 100 Ambrosia 95 95 85 - 75 100 95 95 100 - 85 85 90 Italian pasture 55 - 10 40 - - - - 55 - 60 Soy 100 95 100 - 100 100 100 100 100 - 100 100 100 Surinam grass 80 95 55 - 45 60 90 75 80 - 55 60 65 Alcotán 80 95 80 - 85 90 95 100 95 - 85 90 Wheat 45 - 20 30 - - - - - 35 - - 45 Grass of the wind 70 - 30 45 - - - - - 60 - - 65 Table C Compounds 31 g ai / ha 2 3 9 11 16 17 19 25 30 34 42 47 64 65 post-germination Barley 0 0 - - - - 25 - - 20 - - 20 40 Gram bermuda 15 0 60 0 0 0 5 0 0 - 0 0 20 60 Alopecuro 60 0 - - - - 60 - - 0 - - 40 60 Bromeliad aterilladolada20 20 - - - - 0 - - 0 - - 10 50 Canary seed 30 10 - - - 60 - - 20 - - 5 30 Estelaria 60 0 15 0 0 ~ 0 0 - 40 - 0 0 0 60 Ajonjera 65 60 40 0 75 95 25 85 90 - 0 45 90 100 Corn 15 0 45 0 0"0 0 0 0 - 0 0 20 90 Garranchuelo 40 0 60 0 0 0 40 0 0 - 0 0 70 80 Fluffy button grass 40 0 40 0- 0 0 25 0 0 - 0 0 30 80 Giant bark 0 0 60 0 0 0 5 0 0 - 0 0 0 60 Carricera verde 55 20 - 35 - - 40 - - 0 55 Cuajaleche 0 0 0 0 0 0 0 0 0 - 0 0 35 50 Sorghum of alepo 0 0 55 0 0 0 0 10 0 - 0 - 60 60 Kochia 85 20 95 65 95 100 90 80 55 - 5 0 80 85 Chenopodium 100 75 90 60 95 95 90 60 50 - 10 45 80 90 Morning glory day 70 45 90 0 85 95 55 90 90 - 0 35 90 90 Yellow tigernut 0 0 0 0 0 0 0 0 0 - 0 0 40 0 Wild Oats 20 30 - - - 40 - - 20 5 15 Ashen 65 60 55 70 85 45 50 50 60 - 10 15 85 90 Ambrosia 65 55 70 45 60 65 40 50 60 - 0 0 75 90 Italian Pasture 35 35 - - - 65 - - 40 5 50 Soy 100 60 95 60 ^ 85 85 55 90 80 - 10 40 90 100 Suriname grass 0 0 45 0 0 0 25 0 0 - 0 0_ 20 80 Alcotán 65 25 0 50 55 25 40 20 10 - 0 0 80 80 Wheat 20 0 - - - - 30 - - 0 _ - 0 40 Wind grass 65 10 - - - - 40 - - 40 - - 40 60 Table C Compounds 31 g ai / ha 76 78 79 83 88 94 95 117 129 133 135 136 post-germination Barley - 5 30 - - - - - 40 - 50 Grama bermuda 70 60 - 5 so 70 85 65 - 85 80 Alopecuro - 0 40 _ _. _ _ 45 - 55 Bromelia atercipelada - 5 20 - - - - - 0 - - - Birdseed - 0 20 - - - - - 30 - - 45 Estelaria 45 0 - 0 80 45 - - - 10 15 50 Ajonj era 100 90 - 70 90 80 100 - - 85 100 100 Corn 35 40 - 15 0 35 - 30 - 40 10 35 Garranchue1o 75 55 _ 45 75 80 80 90 - 75 75 75 Leafy button grass 60 50 - 15 70 80 75 80 - 50 60 65 Giant bark 25 0 - 0 55 65 75 55 - 60 60 75 Green barnyard - 25 20 - - - - - 40 - - 65 Cuajaleche 45 0 - 10 50 60 75 40 - 55 35 65 Sorghum of alepo ~ 65: 10 - 55 30 60 75 50 - '85 35 85 Kochia 95 90 - 75 85 90 95 90 - 80 90 80 Chenopodium 95 ~ 90 - 95 90 95 100 95 - 95 90 95 Day glory 95 95 - 85 60 80 80 50 - 90 90 85 Yellow Tigernut "30 0 - 60 40 60 60 50 - 75 0 65 Wild Oats - 5 25 - - - - - 35 - - 45 Ash 95 50 - 95 95 100,100 95 - 85 95 100 Ambrosia 90 70 - 70 90 90 95 95 - 80 80 85 Italian Pasture - 0 35 - - - - - 55 - - 50 Soy 95 90 - 90 100 100 100 100 - 95 - 100 Surinam grass 70 50 - 30 45 60 70 50 - 45 50 65 Alcotán 80 50 - 85 85 90 100 70 - 85 90 85 Wheat - 20 20 - - - - 35 - 40 Grass of the wind - 5 40 - - - - - 45 - - 60 Table C Compounds 500 g ai / ha 11 19 25 47 65 76 79 83 94 95 117 129133 135 post-germination Barley - 25 - - 40 - or - - - - 35 - Gra bermuda 0 0 0 0 60 15 - 0 60 70 60 - 50 40 Alopecuro 55 50 - 20 - - - 35 Bromelia atercipelade L - 0 - - 40 - 0 - - - - 0 - - Bird seed - 45 - - 30 - 0 - - - - 0 - - Estelaria 0 0 0 0. 60 35 - 0 - - 30 - 0 0Ajonj was 0 25 70 35 90 100 - 60 75 100 90 - 75 90 Corn 0 0 0 0 5 10 - 5 10 20 30 - 35 5 Garranchuelc > 0 20 0 0 80 55 - 25 70 75 85 _ 50 65 Button grass L fluffy 0 0 0 0 60"55 15 60 75 '60 - 35 30 Giant bark 0 0 0 0 50 15 0 30 - 50 - 15 10 Green barnyard - 30 - - 50 - 20 - 40 - Cuaj aleche 0 0 0 0 50 30 - 10 35 65 40 - 15 5 Aleppo Sorghum 0 0 0 - 4 455 2 255 - 10 55 70 10 • - 70 15 Kochia 40 80 10 0 0 8 855 9 900 - 65 75 95 90 - 75 75 Chenopodium 50 70 30 0 0 8 855 9 900 - 90 95 100 95 - 95 60 Day glory 0 ~ * 90 20 90 95 70 60 - 20 - 80 80 Yellow tigernut 0 0 0 0 0 10 60 55 60 5 - 60 0 Wild Oats - 40 - - 5 - - 30 - Ash 60 50 50 0 90 85 95 95 95 90 - 85 85 Ambrosia 15 35 40, 0 80 80 - 65 90 95 95 - 80 75 Italian pasture - 65 - 10 - 35 - 45 - Soy 45 45 40 20 100 95 - 85 100 100 100 - - - 95 100 Surinam grass 0 0 0 0 60 60 - 20 50 65 45 - 35 45 Alcotán 20 30 5 0 65 45 - 70 75 95 60 - 80 55 Wheat - 10 - - 40 - 0 - - - - 0 - Wind grass - 40 - - 50 - 40 - - - - 40 - Table C Compounds Table C Compounds 16 g ai / ha 136 8 g ai / ha 95 post-germination post-germination Barley 40 Gram bermuda 70 Gram bermuda 75 Estelaria 95 Alopecuro 40 Ajonjera 100 Velvety Bromeliad 30 Corn 20 Alpiste 40 Garranchuelo 75 Stellia 45 Fluffy button grass 75 Aj onj was 95 Giant Warbler 70 Corn 35 Cuajaleche 50 Garranchue1o 60 Aleppo Sorghum 55 Fluffy button grass 55 Kochia 90 Giant bark 65 Chenopodio 75 Green barnyard 45 Dondiego of day 60 Cuajaleche "50 Yellow Tigernut 55 Sorghum of Aleppo 60 Cenizo 90 Kochia 75 Ambrosia 90 Chenopodium 95 Soya 100 Dondiego of day 65 Pasture of Suriname 55 Yellow Tigernut 60 Alcotán 95 Wild oats 40 Cenizo 90 Ambrosia 75 Italian pasture 45 Soybean 95 Suriname pasture 55 Alcotán 85 Wheat 20 Wind pasture 45 Ashen 90 Ambrosia 90 Soybean 100 Suriname pasture 55 Alcotán 95 Table C Compounds 500 g ai / ha 14 5 8 10 15 22 26 27 28 33 40 49 50 pregerm Grama bermuda 90 95 70 100 0 70 90 0. 0 35 0 70 95 95 Aj onj era 100 100 100 100 100 100 100 95 95 100 95 100 100 95 Maize 70 90 50 75 0 60 65 20 25 0 40 40 65 45 Garranchuelo 95 95 60 0 0 100 100 - 85 - 100 100 100 95 Leafy button grass 95 95 0 100 0 95 95 0 15 0 0 95 25 40 Giant barnacle 90 85 60 0 0 80 60 10 20 0 50 35 65 70 Cuaj aleche 70 65 40 45 0 0 100 0 20 20 0 40 15 0 Aleppo Sorghum 90 95 70 20 0 95 100 100 65 - 40 95 85 85 Kochia 100 100 100 100 65 100 - 50 45 100 50 - 100 90 Chenopodium 100 100 100 100 95 100 100 90 100 100 - 100 100 100 Day glory 100 100 10010010010010010090 100100 95 100100 100 Solano 100 100 100 - 95 100 100 100100100 100 100100 100 Yellow Tigerwort 50 80 0 100 20 95 0 20 0 0 0 0 0 Ash 100 100 100 95 85 100 100 100100100 90 100100 100 Ambrosia 100 100 100 100 85 100 100 90 95100 90 100100 100 Soy 100 100 100 100 - 100 100 20 75 90 90 95 90 90 Sunflower 100 100 100 100 0 100 100 90 95100 90 95 100 100 Suriname pasture .90. 100 0 100 0 95 100 10 30 0 1.0 90 65 85 Alcotán 100 100 90 100 60 100 100 90 70100 85 100100 100 Table C Compounds 250 g ai / hal 2 3 4 5 8 9 10 12 13 15 16 17 22 pregermination Gram bermuda 70 0 0 45 30 100 100 0 20 0 0 0 0 50 Aj onj era 100 100 70 100 100 100 100 0 90 95 100 100 100 100 Corn 50 0 0 75 20 10 75 0 - 30 45 75 75 65 Garranchuelo 90 50 0 85 20 0 100 0 0 0 95 95 80 95 Leafy button grass 90 45 0 95 0 100 100 0 100 0 85 65 85 95 Giant barnyard 90 30 0 75 10 0 80 0 0 5 65 75 75 20 Cuajaleche 10 60 0 55 0 35 50 0 0 0 0 0 0 80 Aleppo sorghum 80 40 0 90 60 0 90 0 5 45 75 80 75 100 Kochia 100 100 30 100 100 100 100 45 85 85 100 100 85 - Quenopodium 100 100 80 100 100 90 100 65 70 90 100 100 100100 Day glory 100 100 35 100 90 100 100 0 90 90 100100 100100 Solano 100 100 20 100 100 - - 20 80 90 100100 100100 Yellow plantain 50 0 0 15 0 100 100 0 0 0 0 0 95 Ashen 100 100 80 100 100 '90- 100- 70 85 90 100100100100 Ambrosia 100 0 45 100 100 100 100 55 85 85 100100100100 Soy 100 100 20 100 98 100 100 - 70 90 95 100100100 Sunflower 100 100 0 100 100 100 100 0 85 90 100100100100 Surinam grass 90 0 0 85 0 100 100 0 0 10 75 80 0100 Alcotán 95 90 35 95 90 100 100 0 70 90 100100 100100 Table C Compounds 250 g ai / ha 26"27 28 30 31 33 40 49 50 64 pre-germination Bermudagrass 0 0 30 0 0 0 0 85 0 20 Ajonjera 90 70 95 90 85 90 90 95 95 30 Corn 0 15 0 0 0 30 20 15 20 30 Garranchuelo - 0 - 85 0 100 - 95 95 90 Fluffy button grass 0 0 1 100 0 0 5 500 0 0 0 0 7 700 20 0 40 Giant barnyard 0 0 0 0 0 0 6 600 0 0 5 500 3 300 0 0 0 Grooming 00 00 00 5500 2200 00 55 0 0 75 Aleppo Sorghum 0 45 0 5 5 10 80 Kochia - 30 90 90 70 50 - 100 20 70 Quenopodium - 90 100 90 80 85 100 100 100 100 Morning glory 85 95 100 100 50 90 90 100 95 10 Solano 100 100 100 100 - 95 100 100 100 95 Yellow tigernut 0 0 0 0 0 0 0 0 0 10 Cenizo 100 90 100 90 40 90 100 100 95 100 Ambrosia 85 85 100 100 60 70 100 1-00 95,100 Soy 10 20 65 70 80 80 90 90 75 85 Sunflower 70 90 100 90 70 80 90 100 95 85 Suriname pasture 10 20 0 20 0 0 10 40 65 90 Alcotán 90 50 95 50 60 60 90 90 85 0 Table C Compounds 125 g ai / ha 1 2 3 4 5 8 9 10 11 12 13 15 16 17 pre-germination Bermudagrass 50 0 0 20 0 100 100 0 0 0 0 0 0 0 Dusky 100 80 55 95 90 85 100 0 0 85 90 90 95 95 Corn 0 - 0 0 5 0 60 0 0 60 10 15 20 35 Garranchuelo60 0 0 65 0 0 95 0 60 0 0 95 65 20 Leafy button grass 60 0 0 80 0 65 95 0 0 10 0 20 15 20 Giant barley 30 0 0 40 0 0 75 0 20 0 0 0 0 20 Cuajaleche 0 0 0 25 0 0 20 0 0 0 0 0 0 0 Aleppo Sorghum 30 0 0 70 20 0 65 0 75 5 5 65 65 55 Kochia 100 95 20 100 95 85 100 0 60 50 80 100 100 25 Quenopodium 100 100 0 100 95 20 100 50 85 40 90 100 100100 Morning glory 100 100 20 100 80 100 100 0 0 60 85 100 100100 Solano 100 100 0 100 100 - - - - 60 90 100 95 95 Yellow Tigernut 0 0 0 0 0 0 100 0 - 0 0 0 0 0 Ashen 100 95 65 100 90 85 100 55 90 50 85 100 100100 Ambrosia 100 0 0 100 90 100 100 0 45 20 70 95 95 95 Soy 100 90 15 100 90 100 100 - 55 - 90 90 100 95 Sunflower 100 100 0 100 90 40 100 0 0 0 60 100 100100 Suriname grass 35 0 0 65 0 100 100 0 100 0 0 65 15 0 Alcotán 90 75 20 95 85 75 100 0 0 50 80 95 95 100 Table C Compounds 125 g ai / ha 19 22 25 26 27 28 30 31 33 40 47 49 50 64 pre-germination Gram bermuda 0 50 10 0 0 20 0 0 0 0 95 0 0 20 Ajonjera 80 95 '85 70 50 95 85 75 0 70 75 95 85 5 Corn 0 50 0 0 10 0 0 0 0 20 0 15 10 20 Garranchuelo 0 95 0 - 0 - 70 0 20 - 100 95 90 70 Leafy button grass 0 95 50 0 0 0 45 0 0 5 0 0 0 0 Giant barley O 15 O O O O 20 O 10 O 20 O 0 O Cuajaleche O O O O O O 35 0 0 0 90 O O O Aleppo Sorghum 55 100 O 20 5 O 5 80 O 65 55 50 Kochia "90 - 70 - O 80 70 50 - - 100100 O 25 Quenopodium 100 100 50 - 40 100 85 40 - 100 95 100 100 95 Morning glory 90 100 90 5"70 100 90 10 85 90 100 95 95 0 Solano 100 100 75 100 70 100 100 0 50 100100 100 100 85 Yellow tigernut 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ashen 95 100 85 100 80 95 80 35 90 100 85 90 90 100 Ambrosia 80 100 85 10 65 95 90 60 20 90 65 100 85 95 Soy 90 95 65 10 0 45 5 15 30 40 0 70 60 85 Sunflower 90 95 90 20 20 50 90 5 70 90 100 75 55 30 Suriname pasture 10 90 40 0 0 0 0 0 0 0 0 15 15 50 Alcotán 65 95 40 10 0 55 15 0 20 70 50 70 75 0 Table C Compounds 125 g ai / ha 65 75 76 77 78 117 135 pregermination Bermuda grass 80 20 0 0 20 65 0 j onj 90 90 90 90 90 90 100 Corn 30 65 45 35 40 25 70 Garranchuelo 80 60 60 0 45 60 ..5 Fluffy button grass 70 60 50 0 10 50 0 Giant barley "60 10 10 0 0 50 0 Milk cell 50 30 0 0 0 30 40 Aleppo sorghum 70 55 50 0 50 70 40 Kochia 70 100 100 80 100 60 100 Quenopodium 100 100 80 40 80- 100 90 Morning glory 100 100 100 75 100 50 100 Solano 80 100 100 0 70 45 50 Yellow tigerberry 70 0 0 0 - 50 0 Ash 100 90 90 65 95 100 100 Ambrosia 100 90 100 55 80 98 70 Soy 100 100 95 100 95 100 100 Sunflower 100 100 100 100 100 100 90 Surinam grass 80 55 45 0 75 95 0 Alcotán 100 100 90 90 80 90 100 Table C Compounds 62 g ai / ha 1 2 3 4 5 8 9 10 11 12 13 15 16 17 pregermination Bermudagrass 0 0 0 0 0 100 100 0 0 0 0 0 0 0 Aj onj era 90 - 30 80 10 - 80 - 0 50 60 65 95 90 Maize 0 0 0 - 5 0 5 0 0 30 5 0 15 20 Garranchuelo10 0 0 40 0 95 0 0 0 Gooseberry grass 0 -0 0 90 0 0 0 0 0 Giant barnyard 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cuaj aleche 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Aleppo sorghum 0 0 0 50 5. 0 45 0 0 0 0 20 40 Kochia 95-90. 0 95 80 50 95 0 0 50 60 95 95 Chenopodium 95 100 0 95 95 0 100 0 40 10 85 95 95 95 Morning glory 90 100 0 100 50 20 100 0 0 60 65 95 95 95 Solano 100 20 0 100 100 - 50 0 95 90 80 Chufa yellow 0 0 100 0 0 0 0 0 0 0 Ash 90 95 50 95 60 65 95 20 65 50 60 90 95100 Ambrosia 95 0 0 100 85 100 100 0 20 10 60 90 90 80 Soy 85 75 0 95 85 100 100 0 - 50 60 75 85 90 Sunflower 80 100 0 100 60 20 100 0 0 0 50 65 85 95 Suriname pasture 0 100 100 0 15 0 0 Alcotán 80 50 0 75 85 65 95 0 60 80 90 80 Table C Compounds 62 g ai / ha 19 22 25 26 27 28 30 31 33 40 47 49 50 64 pregerm Grama bermuda 0 0 0 0 0 0 0 0 0 0 0 0 - 0 Ajonjera 65 90 60 70 0 90 60 60 0 5 70 20 70 0 Corn 0 40 - 0 0 0 0 0 0 0 0 0 - 10 0 Garranchuelo 0 90 0 - 0 - 0 0 0 5 100 95 90 0 Gooseberry grass 0 40 0 0 0 0 5 0 0 5 0 0 0 0 Giant barnyard 0 10 0 0 0 0 0 0 0 0 0 0 0 0 0 Cuaj aleche! 0 0 0 0 0 0 30 0 0 0 85 0 0 0 Aleppo Sorghum 35 80 0 0 0 - 0 0 0 0 0 45 0 5 Kochia 85 - 5 0 0 0 70 0 - - 0 100 - 20 Chenopodium 100 100 30 10 - 95 80 4C Morning glory 90 100 50 0 0 100 85 0 0 - 70 90 80 0 Solano 100 100 30 10 0 100 80 0 0 100 95 95 95 85 Yellow tigernut 0 0 0 0 0 0 0 0 0 0 0 Ash 70 90 35 30 20 80 30 30 Ambrosia 70 90 70 0 20 65 85 10 0 90 45 70 70 85 Soy 85 95 60 0 0 0 5 5 0 10 0 0 0 85 Sunflower 70 90 75 0 0 45 80 0 0 5 20 15 15 0 Surinam grass 0 - 0 0 0 0 0 0 0 - 0 0 0 0 Alcotán 40 90 0 0 50 10 0 0 0 20 15 65 0 Table C Compounds 62 g ai / ha 65 75 76 77 78 95 117"135 pregermination" Gram bermuda 70 0 0 0 0 55 30 0 Ajonj was 50 95 90 80 90 60 5 95 Corn 0 30 35 0 20 5 20 30 Garranchuelo 70 20 5 0 40 35 0 0 Gooseberry grass 5 60 20 0 0 5 15 0 Giant barnyard 50 0 0 0 0 35 5 0 Cuaj aleche. 0 0 0 0 0 40 0 0 Aleppo Sorghum 60 50 20 0 20 80 60 5 Kochia 50 100 95 50 100 45 20 75 Chenopodium 80 80 80 80 100 100 70 Morning glory day 20 95 100 50 85 60 90 Solano - 70 60 60 75 40 35 Yellow tigernut 30 60 50 0 Ash 80 80 80 65 70 100 90 80 Ambrosia 90 80 80 50 80 100 90 35 Soy 95 100 95 100 80 100 100 95 Sunflower 95 100 100 100 100 100 90 90 Surinam grass 80 55 0 0 0 10 50 0 Alcotán 80 85 70 85 70 90 65 90 Table C Compounds 31 g ai / ha 2 3 11 12 13 16 17 19 25 30 31 47 64 pre-germination Bermuda grass 0 0 100 0 0 0 0 0 0 0 0 0 0 0 Aj onj era 60 0 75 0 50 40 45 75 30 20 0 0 0 0 Maize 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Garranchuelo 0 0 20 0 0 0 0 0 0 0 0 0 100 0 Downy button grass 0 0 0 0 0 0 0 0 0 Giant barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Quajaleche 0 0 0 0 0 0 0 0 0 0 0 0 45 0 Sorgo of alepo 0 0 15 0 0 0 0 0 0 0 0 5 Kochia 75 0 95 0 0 45 90 0 0 50 0 20 Quenopodium 90 0 95 0 0 50 95 95 100 0, 0 70 Morning glory 100 0 100 0 30 60 65 70 10 0 0 0 0 0 Solano 0 0 0 55 - 40 0 50 0 85 5 Chufa yellow 0 0 20 0 0 0 0 0 0 0 0 Ash 90 20 95 0 10 50 85 95 45 30 0 10 80 10 Ambrosia 0 0 100 0 45 45 70 55 70 30 5 - 85 Soy 15 0 100 - 0 75 70 25 - 0 0 0 0 Sunflower 20 0 100 0 0 5 20 60 25 60 20 0 0 0 Surinam grass 0 0 95 0 0 0 0 0 - 0 0 0 0 - Alcotán 20 0 70 0 0 60 25 20 35 0 0 0 20 0 Table C Compounds 31 g ai / ha 65 75 76 77 78 95 117 135 pregermination Gram bermuda 50 0 0 0 0 0 0 0 Ajonjera 30 90 90 70 70 0 0 95 Corn 0 0 0 0 0 0 5 30 Garranchuelo 20 10 0 0 5 30 0 0 Grassing button grass 0 0 0 0 0 0 0 0 Giant barley 10 0 0 0 0 30 0 0 Grouper grinder 0 0 0 0 0 10 0 0 Sorghum of alepo 50 0 0 0 10 60 35 0 Kochia 0 80 90 - 80 40 5 75 Chenopodium 50 75 70 0 70 100 100 70 Morning glory day 0 90 60 50 70 10 0 90 Solano 0 50 40 0 30 60 5 30 Yellow tigergrass 0 0 0 0 0 60 0 0 Ash 80 75 80 60 60 100 80 70 Ambrosia 85 70 60 0 65 100 60 - Soy 95 60 70 100 70 100 100 95 Sunflower 70 70 85 50 70 95 50 70 Suriname pasture 40 0 0 0 0 5 40 0 Alcotán 40 60 40 30 55 60 50 85 Table C Compounds 16 g ai / ha 1119 25 47 65 75 76 77 78 95 117 135 pre-germination Bermudagrass 0 0 0 0 0 0 0 0 0 0 0 0 0 Ajonjera 0 15 0 0 0 55 65 55 55 0 0 85 Maize 0 0 0 0 0 - 0 0 0 0 0 5 Garranchuelo 0 0 0 20 0 0 0 0 0 0 0 0 Grass of fluffy button 0 0 0 0 0 0 0 0 0 0 0 0 0 Giant barley 0 0 0 0 0 0 0 0 0 0 0 0 Cuaj aleche 0 0 0 0 0 o. 0 0 0 0 0 0 Sorghum of alepo 0 0 0 0 0 0 0 0 0 50 0 0 Kochia 0 35 0 0 0 70 70 20 70 0 0 60 Chenopodium 0 75 0 0 0 70 70 0 0 100 20 0 Morning glory 0 10 0 0 0 50 40 5 0 0 0 85 Solano - 0 0 80 0 0 30 0 0 0 0 0 Yellow tigernut 0 0 0 0 0 0 0 0 0 40 0 0 Ashen 0 35 0 0 40 70 60 60 55 90 50 70 Ambrosia 0 55 0 0 85 20 50 0 10 90 60 5 Soybean - 0 30 0 85 55 50 40 30 90 85 85 Sunflower 0 10 5 0 40 50 50 20 50 40 0 65 Surinam grass 0 0 0 0 0 0 40 Alcotán 0 25 0 0 0 30 10 10 O * "60 Table C Compounds 8 g ai / ha 95 pregermination Gram bermuda 0 Aj onj era 0 Maíz 0 Garr nchue1o 0 Gooseberry grass 0 Giant barnyworm 0 Milk cork 0 Table C Compounds 8 g ai / ha 95 pregermination Aleppo sorghum 0 Kochia 0 Quenopodio 0 Dondiego by day 0 Solano 0 Yellow tiger 0 Ash 0 Table C Compounds 8 g ai / ha 95 pregermination Ambrosia 65 Soybean 90 Sunflower 5 Surinam pasture 0 Alcotán 0 TEST D Seeds of plant species are selected from gallium (gallium, Galium aparine), common stella (Stellaria media), kochia (Kochia scoparia), chenopodium (Chenopodium album), ash (Amaranthus retroflexus), Russian thistle ( Salsola kali), alforjón (Polygonum convolvulus), wild mustard (Sinapis arvensis), winter barley (Hordeum vulgare), and wheat (Tri ticum aestivum), and are treated before germination with test chemicals formulated in a mixture of non-phytotoxic solvent, which includes a surfactant. At the same time, selected plants of these crop and weed species are treated with post-germination applications of some of the test chemicals formulated in the same manner. The plants vary in height from 2 to 18 cm (stage of 1 to 4 leaves) for treatments after germination. The treated plants and controls are maintained in a controlled growth environment for 15 to 25 days, after which all species are compared to the controls and evaluated visually. The plant response classifications, summarized in Table D, are based on a scale of 0 to 100, where 0 is no effect and 100 is complete elimination. A response with a hyphen (-) means that there are no results in the test.
Table D Compounds 500 g ai / ha of 58 Post-germination Alforjón 100 Galio 100 Kochia 100 Quenopodio 100 Wild Mustard 100 Ash 100 Russian Thistle 80 Wheat 85 Table D Compounds 250 g ai / ha of 26 28 33 35 47 58 Post-germination Barley 50 40 45 70 Alforjon 55 60 55 80 70 100 Estelar 55 65 60 85 70 - Gallium 85 100 65 100 98 100 Kochia 55 75 50 85 75 100 Chenopodium 50 75 45 100 45 100 Wild mustard 75 60 50 75 70 100 Ash 70 70 55 100 65 100 Russian Thistle 40 70 40 100 70 70 Wheat 20 35 45 70 45 70 Table D Compounds 125 g ai / ha 1 2 4 9 26 28 33 35 47 58 Post-germination Barley 45 40 45 65 Alforjón 80 95 100 100 35 55 50 70 65 90 Estelaria 85 85 100 100 45 65 50 80 65 - Gallium 100 100 100 100 70 - 60 100 80 100 Kochia 100 100 100 100 35 75 50 85 65 100 Chenopodium 100 100 100 100 40 70 30 100 40 85 Wild mustard 75 80 90 95 60 60 50 75 65 100 Ashen 100 100 100 100 60 60 55 100 55 100 Russian Thistle 100 100 100 100 40 70 40 100 65 70 Wheat 100 100 100 100 45 35 40 65 35 60 Table D Compounds 62 g ai / ha 1 2 4 9 28 33 35 47 58 Post-germination Barley - - - 20 45 65 - Alforjón 80 90 100 100 35 40 60 65 65 Estelaria 65 85 100 100 65 40 80 60 Gallium 100 100 100 100 100 55 100 75 Kochia 100 100 100 100 70 5 500 8 800 5 500 70 Chenopodium 100 100 100 100 65 3 300 1 10000 3 355 80 Wild Mustard 70 70 75 80 45 50 75 60 100 Ashen 100 100 100 100 60 45 100 50 80 Russian chard 85 95 100 100 65 30 100 55 70 Wheat 90 100 100 90 20 35 0 35 55 Table D Compounds 31 g ai / ha 1 2 4 9 47 Post-germination Alforjon 80 65 85 80 60 Stellia 65 60 100 100 35 Gallium 100 100 100 100 65 Kochia 100 100 100 100 45 Chenopodium 95 100 100 100 35 Wild Mustard 70 65 65 80 55 Ashen 100 85 100 100 35 Russian thistle 65 85 90 90 45 Wheat 80 70 85 80 30 Table D Compounds 16 g ai / ha 1 2 4 Post-germination Barley 50 45. 80 65 Saddlebag 65 60 65 60. Estelaria 9 955 75 100 100 Gallium 9955 75 100 100 Kochia 85 75 85 85 Chenopodium 95 60 95 95 Wild mustard 60 65 65 65 Ashen 60 65 85 65 Russian Thistle 45 65 80 65 Wheat 40 70 80 50 Table D Compounds 500 g ai / ha 58 Post-germination Alforjon 100 Stelar 100 Gallium 100 Kochia 100 Chenopodium 100 Wild Mustard 100 Ash 100 Russian Thistle 85 Wheat 70 Table. D Compounds 250 g ai / ha 26 28 33 35 58 pregermination Barley 35 45 45 45 Alforjon 95 60 65 65 100 Stelar 65 60 65 100 75 Gallium 100 100 100 100 100 Kochia 75 100 65 100 100 Chenopodium 65 60 65 80 100 Wild mustard 65 60 65 75 100 Ash 100 80 90 85 100 Russian chard 100 100 85 100 70 Wheat 35 35 55 50 60 Table D Compounds 125 g ai / ha 1 2 4 9 26 28 33 35 58 pregermination Barley 25 25 35 45 Alforjón 75 85 100 100 65 45 65 60 80 Estelaria 75 90 100 100 60 60 100 Gallium 100 100 100 100 85 100 80 100 100 Kochia 100 100 100 100 55 80 65 100 95 Quenopodium 100 100 100 100 60 60 65 75 100 Wild mustard 90 85 85 85 65 60 65 70 100 Ashen 100 100 100 100 65 - 70 80 100 Russian Thistle 100 100 100 100 _ 80 60 100 65 Wheat 70 70 80 25 35 35 40 50 Table D Compounds 62 g ai / ha 1 2 4 9. 28 33 35 58 Pre-germination Barley 10 10 40 - Alforjón 70 80 100 100 45 55 55 40 Estelar 70 75 85 100 60 - 60 60 Gallium 100 98 100 100 100 70 85 100 Kochia 100 100 100 100 45 60 75 35 Chenopodium 85 95 100 100 60 60 65 60 Wild Mustard 70 70 85 85 60 65 65 65 Ash 95 85 100 100 45 60 65 70 Russian Thistle 100 100 100 100 45 55 85 40 Wheat 70 70 80 75 20 15 35 25 Table D Compounds 31 g ai / ha 1 2 4 9 pregermination Alforjon 60 65 80 85 Estelaria 65 60 70 95 Gallium 80 90 100 100 Kochia 765 70 100 98 Chenopodium 75 85 80 100 Wild mustard 65 70 85 70 Ash 70 70 90 80 Thistle Russian 100 100 100 100 Wheat 70 60 70 75 Table D Compounds 16 g ai / ha 1 2 4 9 pregermination Alforjon 45 45 60 60 Stelar 60 60 65 65 Gallium 80 80 90 85 Kochia 65 55 85 70 Chenopodium 65 - 70 65 Wild mustard 50 50 65 60 Ash 60 65 70 65 Thistle Russian 100 85 90 100 Wheat 35 45 - 60 TEST E Three plastic pots (approximately 16 cm in diameter) per dose are partially filled with black soil of Tama slime that comprises a 35:50:15 ratio of sand, silt and clay, and 2.6% organic matter. . The separate plantings for each of the three pots is as follows. United States seeds of duckweed (Heteranthera limosa), African flowering sedge (Cyperus difformis) and purple amaryllis (Ammannia coccinea) were planted in a 16 cm pot for each dose. Seeds from the United States of flat sedge (Cyperus iría), sprangletop bearded (brdd.) (Leptochloa fusca ssp. Fascicularis), a set of 9 or 10 rice seedlings planted in water (Oryza sativa cv.
'Japónica - M202') and a set of six transplanted rice seedlings (Oryza sativa cv. 'Japónica - M202') are planted in a 16 cm pot for each dose. United States seeds of barnyard weeds (Echinochloa crus-galli), late aquatic weeds (Echinochloa oryzicola), early aquatic weeds (Echinochloa orizoides) and jungle rice (Echinochloa colona) are planted in a 16 cm pot for each dose . The plantations are sequential so that each species of crop and weed is in the stage of 2.0 to 2.5 leaves at the time of treatment. Plants planted in a pot are grown in a greenhouse with day / night temperature settings of 29.5 / 26.7 ° C, and supplementary balanced lighting is provided to maintain a 16-hour photoperiod. The test pots are kept in the greenhouse until the end of the test. At the time of treatment, the test pots are flooded up to 3 cm above the surface of the soil, treated by application of the test compounds directly to the muddy water and then kept at that depth of water for the duration Of the test. The effects of treatments on rice and weeds are visually evaluated by comparison with untreated controls after 21 days. The classifications of plant responses, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete elimination. A response with a hyphen (-) means that there is no result of that test.
Table E Compounds 500 g ai / ha 44 61 62 Flooded land Barnyard weeds 10 65 100 Lentil of water 100 100 100 Flat sedge - 95 100 Jungle rice 20 25 65 Purple amazon 75 100 100 Rice, transplanted 0 25 30 Table E Compounds 500 g ai / ha 44 61 '"62 Flooded land Rice, planted in water 20 35 60 African sedge 100 100 100 Barbed sacate 95 65 75 Early aquatic weed 0 25 0 Late aquatic weed 20 25 20 Table E Compounds 250 g ai / ha 37 44 58 61 62 63 64 65 66 67 69 70 71 72 Flooded land Poultry weeds 0 0 - 0 50 - - 35 40 0 60 0 Lentil water 10 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Flat sedge 90 - 100 40 65 85 100 100 0 60 100 65 0 100 Jungle rice 0 20 0 25 50 30 0 40 0 65 0 0 45 0 Amania purple 80 50 95 100 95 75 80 60 100 85 30 0 30 100 Transplanted Rice 0 0 0 0 0 0 10 0 0 0 0 0 0 0 Rice sown in water 0 0 20 10 10 30 0 10 0 0 0 0 0 0 African sedge 95 100 100 95 100 80 100 100 0 70 100 60 70100 sacate bearded 0 50 60 65 45 65 0 40 0 30 0 0 60 0 Early aquatic weed - 0 - 20 0 0 10 0 0 0 0 0 0 0 Late aquatic weed 0 0 0 20 20 0 20 25 0 0 0 0 0 0 Table E Compounds 250 g ai / ha 73 74 84 88 91 94 95 96 98 99 111117118128 Flooded land Free range 100 0 85 0 10 0 0 0 0 0 0 0 0 0 0 Lens of water 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Flat sedge 45 95 80 100 - 100 0 100 100 100 0 100100 80 Jungle rice 0 65 50 90 70 0 0 0 0 0 0 0 65 10 Purple syrup 100 25 100 65 50 100 80 100 40 45 75 30 85 90 Rice transplanted 0 20 0 10 20 15 20 0 20 0 20 0 0 Rice sown in water 0 0 30 0 20 10 15 10 0 20 0 0 0 0 Sedge African 85 100 100 95 100 100 95 100 60 - 75100100100 Sacate barbado 70 0 40 95 30 40 0 0 0 0 0 0 85 80 Early aquatic weed 0 0 30 50 0 0 0 0 0 0 0 0 0 0 Late aquatic weed 20 0 20 0 0 0 0 0 0 0 0 0 0 0 Table E Compounds 250 g ai / ha 129 133 Flooded land Poultry weeds 0 0 Duckweed 100 100 Flat sedge 100 100 Jungle rice 0 0 Purple amazon 95 85 Rice, transplanted 0 0 Table E Compounds 250 g ai / ha 129 133 Flooded land Rice, sown in water 0 35 African sedge 100 100 Barbed sacate 70 0 Early aquatic weed 0 0 Late aquatic weed 0 0 Table E Compounds 125 g ai / ha 37 44 58 61 62 63 64 65 66 67 69 7071 72 Flooded land Poultry weeds 0 0 - 0 0 - - - 0 40 0 0 0 0 Water lens 100 100 100 100 100 100 100 100 100 100100100100 100 Flat sedge 75 - 100 40 45 85 100 100 0 60 10030 0 100 Jungle rice 0 0 0 20 40 0 0 40 0 30 0 0 0 0 Amania purple 40 20 95 80 85 75 60 50 40 0 0 0 0 35 Transplanted Rice 0 0 0 0 0 0 10 0 0 0 0 0 0 0 Rice planted in water 0 0 0 0 0 20 0 0 0 0 0 0 0 0 Sedge African 65 90 95 85 95 75 100 100 0 40 90 0 30 90 Sacate bearded 0 30 60 60 30 40 0 40 0 30. 0 0 0 0 Early aquatic weed - 0 -? "? 0 0 0 0 0 0 .. 0 0 0 Late aquatic weed 0 0 0 20 20 0- 20 0 0 0 0 0 0 0 Table E Compounds 125 g ai / ha 73 74 84 88 91 94 95 96 98 99 111117118128 Flooded land Free range weeds 90 - 20 0 10 0 0 0 0 0 0 0 0 0 Duckweed 100 100 100 100 100 100 100 100 100 100 100100100100 Flat sedge - 90 60 100 - 100 0 100 100 100 0 10095 60 Jungle rice 0 0 50 0 0 0 0 0 0 0 0 0 65 0 Purple purple 100 20 70 0 30 100 70 100 40 0 30 0 50 90 Transplanted Rice 0 0 0 0 0 10 0 10 0 0 0 0 0 0 Rice sown in water 0 0 0 0 10 10 0 10 0 20 0 0 0 0 African sedge 35 95 90 85 100 100 95 100 60 - 0 100100100 Sacate bearded 50 0 0 85 30 20 0 0 0 0 0 0 70 0 Early aquatic weed 0 0 20 0 0 0 0 0 0 0 0 0 0 0 Late aquatic weed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table E Compounds 125 g ai / ha 129 133 Flooded land Poultry weeds 0 0 Duckweed 100 100 Plain spear 100 95 Jungle rice 0 0 Purple amazon 80 75 Transplanted rice 0 0 Table E Compounds 125 g ai / ha 129 133 Flooded land Rice planted in water African sedge 100 100 Barbed sacate 0 0"Early aquatic weed 0 0 Late aquatic weed 0 0 Table E Compounds 64 g ai / ha 37 44 58 61 62 63 64 65 66 67 69 70 71 72 Flooded land Poultry weeds 0 0 - 0 0 - - - - 0 0 0 0 - Lentil water 100 100 100 100 100 100 100 100 100 100 100100 100100100 Flat shrub 0 - 100 0 0 75 90 100 0 30 100 0 0 100 Jungle rice 0 0 0 20 30 0 0 0 0 0 0 0 0 0 0 Purple amazon 30 10 85 80 85 65 60 30 0 0 0 0 0 25 Planted rice 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice sown in water 0 0 0 0 0 0 0 0 0 0 0 0 0 0 African sedge 50 90 95 75 80 75 85 85 0 0 30 0 0 75 Sacate barbado 0 30 60 35 0 40 0 0 0 0 0 0 - 0 Early aquatic weed - 0 - 0 0 0 0 0 0 0 0 -0 0 0 Late aquatic weed 0 0 0 20 20 -0 0 0 0 0 0 0 0 0 Table E Compounds 64 g ai / ha 73 74 84 88 91 94 95 96 98 99 111 117118128 Flooded land Poultry weeds 0 0 0 0 10 0 0 0 0 0 0 0 0 0 0 Duckweed 100 100 100 100 100 100 100 -100 100 100 85 100100100 Sedge flat 0 0 60 100 - 100 0 100 100 100 0 10095 0 Jungle rice 0 0 0 0 0 0 0 0 0 0 0 0 45 0 Amania purple 90 0 20 0 0 75 30 90 0 - 30 0 30 80 Rice Transplanted 0 0 0 0 0 10 0 0 0 0 0 0 0 0 Rice sown in water 0 0 0 0 10 - 0 0 0 0 0 0 0 0 African sedge 0 80 80 - 30 100 95 100 60 - 0 10010070 Sacate bearded 0 0 0 0 0 0 0 0 0 0 0 0 0 Early aquatic weed 0 0 10 0 0 0 0 0 0 Late aquatic weed 0 0 0 0 0 0 0 0 0 Table E Compounds 64 g ai / ha 129 133 Flooded land Poultry weeds 0 0 Lentil of water 100 100 Flat sedge 100 95 Jungle rice 0 0 Purple amazon 75 65 Transplanted rice 0 0 Table E Compounds 64 g ai / ha of 129 133 Flooded land Rice planted in water 0 0 African sedge 80 95 Bearded sacate 0 0 Early aquatic weed O O Late aquatic weed O O Table E Compounds 32 g ai / ha 37 44 58 61 62 63 64 65 6'6. 67 69 70 71 72 Flooded land Corral weeds 0 - "0 - 0 0 - - - 0 0 0 0 0 0 Duckweed 100.100 100 100 100 30 100 100 100100100 40 10080 Flat sedge 0 - 100 0 0 75 85 80 0 0 70 0 0100 Jungle rice 0 0 0 0 20 0 0 0 0 0 0 0 0 0 Amania purple 0 0 80 65 75 65 60 30 0 0 0 0 0 25 Transplanted Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice planted in water 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 African sedge 50 20 95 20 70 75 80 80 0 0 0 0 0 30 Sacate bearded 0 20 40 35 0 0 0 0 0 0 0 0 0 0 Early aquatic weed - 0 - 0 0 0 0 0 0 0 0 0 0 0 0 Late aquatic weed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5. Table E Compounds 32 g ai / ha 7374 84 88 91 94 95 96 98 99 111 117 118128 Flooded land Weed of 0 pen - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Lens of water 100 100 100 100 100 100 100 100 100100 0 100100100 Flat sedge 0 0 35 85 - 100 0 100 80 - 0 100 95 0 5 jungle rice 0 0 0 0 0 0 0 0 0 0 0 0 40 0 Amania purple 0 0 20 0 0 65 - 85 0 0 20 0 20 75 Transplanted Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice planted in water 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 African sedge 0 0 80 40 0 100 95 100 60 - 0 85 95 60 Sacate bearded 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Early aquatic weed O O O O O O O O O Late aquatic weed O O O O O O O O Table E Compounds 32 g ai / ha 129 133 Flooded land Poultry weeds 0 0 Duckweed 100 100 Flat sedge 100 65 Jungle rice 0 0 Purple amazon 60 20 Transplanted rice 0 0 Table E Compounds 32 g ai / ha 129 133 Flooded land Rice planted in water 0 0 African sedge 60 0 Bearded sake 0 0 Early aquatic weed 0 0 Late aquatic weed 0 0 Table E Compounds 16 g ai / ha 37 58 63 64 65 66 67 69 70 71 72 73 74 84 Flooded land Weed of .corral or - - - - 0 0 0 0 0 - 0 0 0 Duckweed 80 100 30 100 100 95 85 95 0 100 80 75100100 Flat sedge 0 40 60 75 0 0 0 65 0 0 90 0 0 25 Jungle rice 0 0 0 0 0 0 0 0 O 'O O O O O Germany "purple 0 60 65 20 0 0 0 0 0 0 0 0 0 0 Transplanted Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice planted in water 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Juncia africana 30 65 70 65 20 0 0 0 0 0 0 0 0 70 Sacate bearded 0 20 0 0 0 0 0 0 0 - 0 0 0 0 Early aquatic weed - - 0 0 0 0 0 0 0 0 0 0 0 0 Late aquatic weed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Table E Compounds 16 g ai / ha 88 91 94 95 96 98 99 111 117 118128129 133 Flooded land Poultry weeds 0 0 0 0 0 0 0 0 0. 0 0 0 0 Duckweed 95 100 100 100 100 0 .95 0 .100 100 95 100 100 Flat sedge 50 - 100 0 100 80 100 0 100 85 0 100 30 Jungle rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Purple Germany 0 0 0 30 0 0 0 0 0 0 0 30 0 Transplanted Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 Rice sown in water 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge African 40 0 100 0 100 60 - 0 60 85 0 0 0 Sacate bearded 0 - 0 0 0 0 0 0 0 0 0 0 0 Early aquatic weeds 0 0 0 0 0 0 0 0 0 0 0 0 0 Late aquatic weed 0 0 0 0 0 0 0 0 0 0 0 0 0 TEST F Seeds or small nuts of plant species selected from bermudagrass (grass) (Cynodon dactylon), blue weed (Poa pratensis), agrostis (Agrostis palustris), laston (Festuca ovina), crabgrass - (Digitaria sanguinalis ), cuajeleche (Eleusine indica), dallisgrass (Paspalum dilatatum), annual blue weed (Poa annua), common stella (Stellaria media), syrup (Taraxacum officinale), white clover (Trifolium repens) and yellow tiger nut (Cyperus esculentus) are planted and treat before germination with the cloudy test substance formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, selected plants of these crop and weed species are treated with post-germination applications of the test chemicals formulated in the same manner. The plants are classified in height from 2 to 18 cm (stage of 1 to 4 leaves) for post-germination treatments. The treated plants and controls are kept in a greenhouse for 12 to 14 days, after which all species are compared with the controls and evaluated visually. The response ratings of the plants, which are summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete elimination. A response with a hyphen (-) means that there is no result in the test.
Table F Compound Table F Compound Table F Compound 500 g ai / ha 1 250 g ai / ha 1 125 g ai / ha 1 Post-germination Post-germination Post-germination Agrostis 70 Agrostis 50 Agrostis 50 Bermuda grass, Bermuda grass, Bermuda grass, grass 70 grass 50 grass 40 Blue weeds 95 Blue weeds 70 Blue weeds 45 Blue weeds, Blue weeds, Blue weeds, -Kentucky 30 Kentucky 0 Kentucky 0 Stelaria 100 Stelaria 85 Stelaria 85 White clover 100 White clover 100 White clover 100 Garranchue1o 90 Garranchuelo 75 Garranchuelo 70 Dallisgrass 60 Dallisgrass 75 Dallisgrass 15 Almirón 95 Almirón 85 Almirón 75 Lastón 0 Lastón 0 Lastón 0 Cuaj leche 50 Cuajaleche 40 Cuajaleche 35 Yellow tigernut 15 Yellow tigernut 15 Yellow tigernut 10 Table F Compound Table F Compound Table F Compound 62 g ai / ha 1 31 g ai / ha 1 500 g ai / ha 1 Post-germination Post-germination Post-germination Agrostis 30 Agrostis 0 Agrostis 100 Bermuda grass, Bermuda grass, Bermuda grass, turf 20 grass or grass 90 Blue weeds, Kentucky O Blue weeds 35 Blue weeds 70 Stelaria 80 Blue weeds Blue weeds Kentucky 20 Kentucky 80 White clover 90 Estelaria 0 Estelaria 100 Big crab 45 White clover 70 White clover 100 Dalis 0 Crabgrass Big crab 0 large 100 Almirón 75 Dalis 0 Dalis 95 Lastón 0 Almirón 50 Almirón 100 Cuajaleche 10 Lastón 0 Lastón 90 Yellow Tigernut 10 Cuaj aleche 5 Cuajaleche 85 Yellow Tigernut 0 Yellow Tigernut 70 Table F Compound Table F Compound Table F Compound 250 g ai / ha 1 125 g ai / ha 1 62 g ai / ha 1 Pre-germination Pre-germination Pregermination Agrostis 90 Agrostis 60 Agrostis 60 Bermuda grass, Bermuda grass, Bermuda grass, grass 80 grass 50 grass 40 Blue weed 70 Blue weed 45 Blue weed 65 Blue weed, Blue weed, Blue weed, Kentucky 40 Kentucky 30 Kentucky 30 Estelaria 100 Estelaria 100 Estelaria 100 White clover 100 White clover 100 White clover 100 Garranchuelo 95 Garranchuelo 85 Garranchuelo 40 Dalis 70 Dalis 45 Dalis 35 Almirón 100 Almirón 100 Almirón 95 Lastón 60 Lastón 60 Lastón 60 Cuaj aleche 65 Cuaj aleche 3.0 Cuaj aleche 40 Yellow Tigernut 25 Yellow Tigernut 30 Yellow Tigernut 15 Table F Compound Table F Compound Table F Compound 31 g ai / ha 1 31 g ai / ha 1 31 g ai / ha 1 Pre-germination Pre-germination Pregermination Agrostis 50 Stellia 80 Almirón 35 Bermuda grass, grass 10 White clover 80 Lastón 50 Blue weed 20 Garranchuelo big 15 Cuajaleche 30 Blue weed, Kentucky 0 Dalis 10 Yellow tiger grass 0 TEST G Small seeds or nuts of plant species selected from Bermuda grass are sown (Cynodon dactylon), Surinam grass (Brachiaria decumbens), large crabgrass (Digitaria sanguinalis), green carrion (Setaria viridis), cuajaleche (Eleusine indica), Aleppo sorghum (Sorghum halepense), kochia (Kochia scoparia), morning glitter (Ipomoea lacunosa), purple tiger nut (Cyperus rtundus), common ragweed (Ambrosia elatior), black mustard (Brassica nigra), panic (Panicum máximum), dalis (Paspalum dilatatumj, barnyard weed (Echinochloa crus-galli), southern mulberry grass (Cenchrus echinatus), common looper (Sonchus oleraceous), spiny aids (Sida spinosa), Italian grass (Lolium multiflorum), common purslane (Portulaca olerácea), broad-leaved brachiaria (Brachiaria platyphylla), cana weed (Senecio vulgaris), common stelaria (Stellaria media), tropical cornelina (Commelina benghalensis), annual blue weed (Poa annua), velvety bromeliad (Bromus tectorum), treadmill (ottJboellia cochinchinensis), red grass (Elytrigia repens), erigeron of the glen (Conyza canadensis), field bindweed (Convolvulus arvensis), bidente (Bidens bipinnata), common mallow ( Malea sylvestris) and Russian thistle (Salsola kali) and are treated before germination with the test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. At the same time, the selected plants of these weed species were treated with applications subsequent to the germination of some of the test guanine substances formulated in the same way. The plants varied in width from 2 to 18 cm (stage of 1 to 4 leaves) for post-germination treatments. The treated plants and controls were kept in a greenhouse for 12 to 21 days, after which time all the species were compared to controls and visually evaluated. At a different time, grape vines (Vitus vinifera), which grew in an established container and olive (Olea europea) and orange (Ci trus sinensis) trees with "some of the test chemical substances formulated in the same way, were treated. and were applied to the soil surface and in the lower 5 cm of the vines or plant trunks (post-directed application) .The plants varied in height from 30 to 100 cm.The applications were made using a manual sprinkler that supplied a volume of 990 1 / ha The treated plants and controls were kept in a greenhouse for 28 days, after which the treated plants were compared with the controls and visually evaluated, and seeds were also planted at a different time ( nodes) of sugarcane (Saccharum officinarum) and were treated before germination and / or after germination with some of the test chemicals formulated in the same manner. Treated plants and controls were kept in a greenhouse for 14 days, time after which the treated plants were compared with controls and visually evaluated. The plant response classifications, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete elimination. A response with a hyphen (-) means that it is not a test result.
Table G Compounds Table G Compounds 500 g ai / ha 1 375 g ai / ha 1 Post-germination Post-germination Weed stock 75 Weeds of stock 70 Gram bermuda 50 Gram bermuda 40 Correhuela 95 Correhuela 95 Black mustard 75 Black mustard 75 Blue weed 50 Blue weed 50 Velvety bromeliad 80 Velvety bromeliad 70 Big crab 70 Stela 100 Dalis 30 Big crab 70 Green bream 60 Dalis 30 Catchhouse 60 Green bream 50 Herb cane 100 Cuaj alache 60 Panic 95 Herb cane 100 Erigeron 100 Erigeron 100 Treadmill 70 Treadmill 60 Aleppo Sorghum 95 Aleppo Sorghum 95 Malva 95 Kochia 95 Day glory 100 Malva 95 Purple Chufa 30 Morning glory day 100 Spiny AIDS 95 Purple Chufa 30 Verdolaga 100 Spiny Aida 95 Red Gramilla 70 Verdolaga 100 Ambrosia 100 Colored Gramilla 70 Italian Pasture 40 Ambrosia 100 Herbamora 95 Russian Thistle 100 Brachyaria 85 Italian Pasture 40 Cerraj to '100 Herb Grass 95 Bidente 95 Brachyaria 75 Cornelina 95 Cerraj to 95 Grass of Suriname 90 Bidente 95 Cornelina 95 Pasture Surinam 90 Table G Compounds Table G Compounds 250 g ai / ha 1 22 77 125 g ai / ha 1 Post-germination Post-germination Barnyard weeds 70 85 75 Barnyard weeds 60 Bermuda grass 40 65 50 Bermuda grass 25 Correhuela 95 100 100 Correhuela 95 Black mustard 75 95 60 Black mustard 75 Blue weed 40 75 40 Blue weed 30 Velvety Bromeliad 60 95 75 Velvety Bromeliad 30 Estelaria 95 95 100 Estelaria 95 Big crab 70 85 75 Big crab 60 Dalis 30 75 50 Dalis 20 Green Carricera 30 75 40 Green Carricera 20 Cuajaleche 60 50 65 Cuajaleche 60 Hierba cana 95 - 100 Hierba cana 95 Panic 95 100 75 Panic 70 Erigeron 100 - 80 Erigeron 70 Treadmill 60 85 80 Treadmill 40 Sorghum of Aleppo 95 - 85 Sorghum of Aleppo 70 Kochia - 100 98 Malva 60 Malva 70 95 95 Morning glory 100 Day glory 100 100 100 purple Chufa 10 Purple Chufa 20 15 40 Spiny Aida 70 Spinous AIDS 90 95 80 Verdolaga 100 Verdolaga 100 98 85 Gramilla colorada 30 Gramilla colorada 60 85 60 Ambrosia 95 Ambrosia 95 100 100 Russian thistle 100 Russian Thistle 100 100 - Italian Pasture 10 Italian pasture 40 85 40 Hierbamora 60 Hierbamora 95 95 40 Braquiaria 60 Braquiaria 75 85 70 Cerraj a 95 Cerraja 95 100 95 Bidente 95 Bidente 95 - 98 Cornelina 95 Cornelina 95 98 100 Pasture of Suriname 60 Suriname pasture 85 95 70 Table G Compounds Table G Compounds 125 g ai / ha 22 77 62 g ai / ha 1 22 6477 Post-germination Post-germination Weeds 25 65 Barnyard weeds 60 15 2040 Bermuda grass 40 35 Bermuda grass 25 35 3535 Morning glory 100 100 Morning glory 90 100 9098 Black mustard 95 60 Black mustard 60 75 1050 Blue weed.,. 40 40 Blue weed 20 15 0 0 Velvety Bromeliad 95 65 Velvety Brcmelia 3085 75 35 Estelaria 85 90 Estelaria - 50 - 90 Big crab 85 75 Big crab 50 50 8075 Dalis 25 35 Dalis 10 15 2015 Green barnyard 50 40 Green barnyard 10 25 0 35 Cuajaleche 35 50 Cuajaleche 20 25 2050 White grass 85 95 White grass 60 65 0 80 P 95 95 65 Panic 60 65 0 65 Erigeron - 80 Erigeron - - 6075 Treadmill 75 70 Treadmill 20 50 6065 Aleppo Sorghum - 85 Aleppo Sorghum 70 - 0- 70 Kochia 100 98 Kochia - 98 9098 Malva 85 85 Malva 50 - 9080 Dondiego of day 95 100 Dondiego of day 100 85 6590 Purple Chufa 0 0 Purple Chufa - 0 35 0 Spiny Aida 95 80 Spiny Aphid 70 90 7580 Verdolaga 95 70 Verdolaga 80 85 6060 Red Gramilla 7 755 6 600 Red Gramilla 10 65 3540 Ambrosia 98 98 Ambrosia 75 98 10095 Russian Thistle 100 Russian Thistle 100 100 - Italian Paste 40 30 Italian Pasture 0 15 3530 Hierbamora 85 35 Hierbamora 30 40 2010 Braquiaria 50 60 Branquiaria 20 25 3050 Close to 100 95 Cerraj to 95 95 8090 Bidente - 98 Bidente 80 - 9098 Cornelina '95 90 Cornelina 95 85 9075 Suriname pasture 65 65 Suriname pasture 30 35 10 25 Table G Compounds Table G Compounds 31 g ai / ha 22 64 77 16 g ai / ha 22 64 77 Post-germination Post-germination Poultry weeds 0 20 10 Poultry weeds 0 20 0 Bermudagrass 35 35 20 Bermudagrass 15 20 10 Morninggrass 100 80 98 Morninggrass 85 70 70 Black mustard 75 0 40 Black mustard 50 0 25 Blue weed 0 0 0 Blue weed 0 0 0 Velvety Brsmelia 65 40 20 Velvety Bresmelia 15 20 0 Estelaria 50 - 80 Estelaria - - 10 Gsürranchuelo grande 35 70 70 Gaxranchuelo grande 15 50 60 Dalis 0 0 0 Dalis 0 0 0 Carricera verde 15 0 0 0 Carricera verde 0 0 0 Cuaj aleche 15 0 15 Cuajaleche 5 0 0 Grass cana 65 0 75 Grass cana 65 0 40 Panic 55 0 0 0 Single 5 0 0 Erigeron 60 50 Erigeron - 60--40 Treadmill 25 0 35 Treadmill 15 0 0 Aleppo Sorghum 0 65 - Aleppo Sorghum - 0 20 Kochia 98 85 95 Kochia 98 75 90 Malva 60 90 75 Malva 40 80 65 Dondiego of day 85 20 60 Dondiego of day 50 0 50 Purple Chufa 0 35 0 Purple Chufa 0 35 0 Spinous AIDS 85 75 75 Spinous AIDS 75 65 -70 Verdolaga 55 0 20 Verdolaga 50 0 20 Gramilla colorada 40 20 10 Gramilla colorada 15 20 0 Ambrosia 85 100 75 Ambrosia 65 75 75 Russian Thistle 100 - - Russian Thistle 95 - - Italian Pasture 5 20 20 Italian Pasture 0 10 0 Hierbamora 15 20 0 Hierbamora 0 0 0 Braquiaria 15 0 30 Braquiaria 5 0 0 Cerr j a 85 80 90 Cerraj a 75 80 75 Bidente - 90 95 Bidente - 75 75 Cornelina 40 80 50 Cornelina 15 80 10 Suriname pasture 15 0 10 Suriname pasture 0 0 0 Table G Compounds 8 g ai / ha 64 Post-germination Weeds 0 Gram Bermuda 0 Morning Glory 60 Black mustard 0 Blue weed O Velvety bromeliad 0 Big crab 30 Dalis 0 Green Carricera 0 Cuajaleche 0 Yellow grass 0 Panic 0 Erigeron 60 Treadmill 0 Sorghum of Aleppo 0 Kochia 65 Malva 65 Morning glory 0 Purple rice 0 Spiny Aid 40 Verdolaga 0 Colored Gramilla 0 Ambrosia 75 Italian Pasture 0 Hierbamora 0 Braquiaria 0 Cerraja 65 Bidente 65 Cornelina 65 Pasture of Suriname Table G Compounds 1500 g ai / ha 1 4 Post Address 100 100 grape Olive 50 Orange 50 75 Table G Compounds 900 g ai / ha 4 Posts Olive Address 50 Table G Compounds 500 g ai / ha 1 9 Postsgermination Sugar cane 38 17 Table G Compounds 250 g ai / ha 1 9 Post-germination Sugar cane 13 7 Table G Compounds 125 g ai / ha 1 9 Post-germination Sugar cane Table G Compounds 62 g ai / ha 1 9 Post-germination Sugar cane 0 0 Table G Compounds 31 g ai / ha 1 9 Post-germination Sugar cane 0 Table G Compounds Table G Compounds 500 g ai / ha 1 4 9 375 g ai / ha 1 Pregermination Pregermination Weed stock 70 100 95 Stock weed 70 Bermuda grass 70 100 100 Bermuda grass 70 Correhuela 100 100 100 Correhuela 100 Black mustard 100 100 100 Black mustard 100 Blue weed 85 100 100 Velvety bromeliad 95 Velvety bromeliad 95 100 100 Estelaria 100 Estelaria 100 100 100 Big crab 90 Big crab 90 100 100 Dalis • 95 Dalis 95 100 100 Green barnyard 90 Green barnyard 90100 100 Grooming 50 Grooming 50 90 95 Ginger grass 100 Ginger grass 100 100 - Panic 100 Panic 100 100 100 Erigeron 100 Erigeron 100 100 100 Walker 85 Walker 90 95 85 Sorghum Aleppo 75 Sorghum Aleppo 75 95 95 Kochia 100 Kochia 100 - Malva 95 Malva 95 100 100 Morning glory 100 Day glory 100 100 100 Purple snapper 10 Purple bulrush 100 100 Thorny spinach 100 Spiny spinach 100 100 100 Purslane 100 Purslane 100 100 - Gramilla colorada 95 Colored Gramilla 95 100 100 Ambrosia 100 Ambrosia 100 100 100 Russian Thistle 100 Russian Thistle 100 100 Italian Pasture 95 Italian pasture 95 100 80 Hierbamora 85 Hierbamora 85 100 95 Braquiaria 75 Braquiaria 95 95 100 Cerraja 100 Cerraj a 100 100 - Bidente 100 Bidente 100 100 100 Cornelina 100 Cornelina 100 100 100 Suriname grass 95 Suriname grass 100 95 90 Table G Compounds 250 g ai / ha 1"4 9 22 77 Pregermination pen 50 80 85 80 90 Gram Bermuda YO 95 95 30 60 Morning Glory 100 100 100 100 100 Black mustard 85 100 100 75 95 Blue weed 85 80 95 60 40 Velvety bromeliad 95 100 70 75 75 Estelaria 95 100 100 100 100 Big crab 90 100 90 80 90 Dalis 50 95 80 50 85 Green barnyard 50 100 100 20 90 Cuaj aleche 50 70 95 0 55 Hierba cana 100 100 - 50 100 Panic 85 100 100 95 95 Erigeron 100 100 100 - 100 Treadmill 80 80 80 65 90 Sorghum from Aleppo 60 85 95 80 95 Kochia 100 _ _ 100 100 Malva 95 100 100 80 80 Morning glory 100 100 100 90 100 Purple Chufa 100 100 - 50 100 Spiny Aid 100 100 100 95 95 Purslane 95 100 - 75 100 Colored seed 90 100 70 30 80 Ambrosia 100 100 100 100 100 Russian Thistle 100 100 - 100 100 Italian pasture 30 100 75 50 75 Hierbamora 70 90 90 85 100 Braquiaria 75 95 80 80 95 _ Cerraja 100 100 - 100 100 Bidente 100 100 100 Cornelina 100 100 100 100 100 Suriname Grass 95 80 80 90 100 Table G Compounds 125 g ai / ha 1 4 9 22 77 Pre-germination Barnyard weeds 2 200 7 700 7 700 7 700 8 855 Bermuda grass 2 200 9 900 9 955 0 0 1 100 Morning glory 1 10000 1 10000 1 10000 9 900 1 100 (0 Black mustard 8 800 9 955 7 755 6 655 9 900 Blue weed 3 300 6 600 3 300 3 300 2 200 Velvety bromeliad 2 200 7 700 5 500 2 200 1 100 Estelaria 95 100 100 90 10C Garranchuelo grande 30 75. 90 80 85 Dalis 10 50 70 40 30 Green barnyard 10 70 85 10 85 Cuajaleche 60 60 0 25 Hierba cana "100 95 80 Panic 70 95 100 90 85 Erigeron 95 100 100 - 1 10000 Treadmill 30 70 60 4400 8855 Aleppo Sorghum 40 7 755 8800 5500 8855 Kochia 100 - - 110000 110000 Malva 80 100 100 80 100 Morning glory 100 100 100 90 100 Purple Chufa 100 100 __. 40 100 Thorny AIDS 100 100 100 80 90 Verdolaga 60 100 70 100 Gramilla colorada 60 90 20 50 Ambrosia 95 100 100 95 100 Russian Thistle 100 100 - 100 Italian Pasture 10 60 50 0 40 Hierbamora 30 80 80 70 100 Braquiaria 70 70 80 10 90 Cerraj to 100 100 100 100 Bidente 100 100 100 Cornelina 100 100 100 100 95 Suriname pasture 95 60 70 35 90 Table G Compounds 62 g ai / ha 1 4 22 64 77 Pre-germination Poultry weeds 0 5.0 30 30 10 75 Gram bermuda 10 20 10 0 0 0 Correhuela 95 100 '95 90 65 95 Black mustard 30 95 70 60 35 85 Blue weed 10 10 10 0 0 5 Velvety bromeliad L 00 30 10 0 0 0 Estelaria 70 100 - - 0 90 Garranchuelo grande 20 60 70 40 35 80 Dalis 0 0 10 0 0 15 Green barnyard 10 20 20 0 0 65 Cuajaleche 0 10 10 0 0 5 Grass cane 60 95 - - 40 - Panic 70 95 90 75 0 85 Erigeron 95 100 100 - 95 100 Treadmill 10 70 30 20 20 45 Sorghum from Aleppo 20 60 40 20 0 75 Kochia 100 - - 98 15 95 Mallow 50 100 90 75 0 50 Morning glory 95 100 70 60 0 100 Purple Chufa 10 40 - 30 0 100 Spiny AIDS 70 85 95 65 50 85 Verdolaga 10 60 - 50 35 75 Red Gramilla 10 60 70 20 0 10 Ambrosia 50 80 95 90 95 100 Russian Thistle 100 - - 95 0 100 Italian Pasture 0 30 20 0 0 0 Hierbamora -0 30 - 0 0 100 Brachyaria 10 50 20 0 0 75 Cerraj a 95 100 - 90 90 100 Bidente 100 100 100 - 35 - Cornelina 170 100 100 95 90 95 Suriname grass 95 30 40 0 0 70 Table G Compounds Table G Compounds 31 g ai / ha 22 64 77 16 g ai / ha 22 6477 Pre-germination Pre-germination Poultry weeds 20 0 55 Poultry weeds 10 0 50 Gram Bermuda 0 0 0 Gram Bermuda 0 0 0 Gruel 75 0 90 Gruel 65 0 80 Black mustard 35 20 60 Black mustard 30 0 60 Blue weed 0 0 0 Blue weed 0 0 0 Velvety brsmelia 0 0 0 Velvety brsmelia 0 0 0 Estelaria 50 0 70 Estelaria 0 - -Garranchuelo grande 40 0 45 Garranchuelo grande 0 0 45 Dalis 0 0 5 Dalis 0 0 0 Green barnyard 0 0 5 Green barnyard 0 0 0 Cuaje aleche 0 0 5 Cuajaleche 0 0 0 Grass cana 0 10 60 Grass cana - 0 50 Panic 35 0 75 Panic 0 0 30 Erigeron - 95 90 Erigeron - 75 70 Treadmill 0 0 10 Treadmill 0 _ 0 0 Sorghum of Alepó 0 0 65 Sorghum of Aleppo 0 0 10 Kochia 70 10 95 Kochia 35 0 85 Malva 50 0 40 Malva 50 - 30 Dondiego of day 50 0 90 Dondiego of day 20 0 70 Purple Chufa 0 0 100 Purple Chufa 0 0 100 Spiny Aid 50 30 75 Spinous Aid 50 0 70 Purslane 0 0 60 Purslane 0 0 45 Gramilla colorada. 0 0 0 Red flower 0 0 0 Ambrosia 75 65 95 Ambrosia 65 65 80 Russian Thistle 75 0 - Russian Thistle 65 - 85 Italian pasture 0 0 0 Italian pasture 0 0 0 Hierbamora 0 0 20 Hierbamora 0 0 0 Braquiaria 0 0 10 Braquiaria 0 0 5 Cerraj to 75 35 100 Cerraj to 35 0 80 Bidente - 0 - Bidente - 0 - Cornelina 50 75 85 Cornelina 0 50 60 Suriname pasture 0 0 5 Suriname pasture 0 0 0 Table G Compounds Table G Compounds 8 g ai / ha 64 8 g ai / ha 64 Pregermination Pregermination Weeds 0 Kochia 0 Gram Bermuda 0 Mallow 0 Morning Glory 0 Morning glory 0 Black mustard 0 Purple tiger grass 0 Blue weed 0 Spiny Aid 0 Velvety Bromeliad 0 Verdolaga 0 Estelaria 0 Red Grampilla 0 Garranchuelo grande0 Ambrosía 0 Dalis 0 Russian Thistle 0 Green Carricera! 0 Italian Pasture 0 Cuajaleche 0 Grass Mora 0 Grass cana 0 Braquiaria 0 Panic 0 Cerraja 0 Erigeron 0 Bidente 0 Treadmill 0 Cornelina 0 Aleppo Sorghum 0 Surinamegrass 0 Table G Compounds Table G Compounds 375 g ai / ha 1 125 g ai / ha 1 Pre-germination Pre-germination Sugar cane 0 Sugar cane 0 Table G Compounds Table G Compounds 250 g ai / ha 1 62 g ai / ha 1 Pre-germination Pre-germination Sugar cane 0 Sugar cane 0 TEST H This test evaluates the mixing effect of the -compound 1 with diflufenzopir on several plant species. The seeds of the test plant consisting of large crabgrass (DIGSA, Digitaria sanguinalis (L.) Scop.), Chenopodium (CHEAL, Chenopodium album) were planted in pots.
L.), red-rooted ash (AMARE, Amaranthus retroflexus L.), red-necked ash (SANST, Xanthium strumarium L.), barnyard grass - (ECHCG, Echinochloa crus-galli (L.) Beauv), corn (ZEAMD, Zea mays L. cv. "Pioneer 33G26"), Scarlet day butter (red) (IPOCO, Ipomoea coccinea L.), giant warbler (SETFA, Setaria faberi Herrm.) And Alcotán (ABUTH, Abutilon theophrasti Medik.) In pots containing medium for Redi-Earth ™ planted (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum marsh moss, vermiculite, moisturizing agent and starting nutrients. The seeds of the small seed species are planted at a depth of approximately 1 cm; Larger seeds are planted at a depth of approximately 2.5 cm. Plants are grown in a greenhouse using supplemental lighting to maintain a photoperiod of approximately 14 hours; Daytime and nighttime temperatures are approximately 25-30 ° C and 22-25 ° C, respectively. Balanced fertilizer is applied through the irrigation system. The plants are grown for 7 to 11 days so that at the time of treatment the plants have a height that varies from 2 to 18 cm (stage of 1 to 4 leaves). The treatments consist of compound 1 and diflufenzopyr alone and in combination, suspended or dissolved in an aqueous solvent comprising glycerin and non-ionic surfactant Tween and applied as a foliar spray using a volume of 541 1 / ha. Each treatment doubles four times. It is observed that the application solvent has no effect compared to the untreated verified plants. The treated plants and controls are kept in the greenhouse and water is applied as needed with care not to wet the foliage during the first 24 hours after treatment. Effects on plants approximately 3 weeks after treatment are compared visually with untreated controls. The response ratings of the plants are calculated as the means of four duplicates, based on a scale of 0 to 100 where 0 is no effect and 100 is complete elimination. The Colby equation is used to determine the expected herbicidal effects of the mixtures. The Colby equation (Colby, SR "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 15 (1), pp. 20-22 (1967)) calculates the expected additive effect of the herbicidal mixtures and for two active ingredients is of the form: where Pa + _, is the percent of the effect of the expected mixture of an additive contribution of the individual components, Pa is the observed effect percent of the first ingredient at the same rate of use as in the mixture , and Pb is the observed effect percent of the second active ingredient at the same usage rate as in the mixture. The results and the expected additive effects of the Colby equation are included in table H.
Table H - Observed and expected results of compound 1 alone and combined with diflufenzopyr * * Application rates are in grams of active ingredient per hectare (g a.i./ha). "Obsd" is observed effect. xp. "is the expected effect calculated from the Colby equation.As can be seen from the results included in table H, most of the observed results are greater than expected from the equation of Colby and in some cases much larger It is more noticeable that there is a greater effect than the additive observed in crabgrass, poultry weeds, maize and giant carrion, the increase is less noticeable for other test species, but mainly because the effect It is almost close to 100% at the rates tested.
TEST I This test evaluates the effect of the mixtures of compound 9 with methylsulfuron-methyl and with a 5: 1 by weight combination of chlorsulfuron and metsulfuron-methyl in various plant species. The seeds of the test plants consist of wheat (TR2AW, Triticum aestivum), alforjón (POLCO, Polygonum convolvulus), red root ash (AMARE, Amaranthus retro flexus), wild mustard (SINAR, Sinapsis arvensis), gallium (GALAP; Galium aparine), Russian thistle (SAKR; Salsola kali), common stella (STEME; Stellaria media), kochia (KCHSC; Kochia scoparia) and chenopodium (CHEAL; Chenopodium album) in a combination of black soil and sand. Plants are grown in a greenhouse using supplemental lighting to maintain a photoperiod of approximately 14 hours; Daytime and nighttime temperatures are approximately 23 ° C and 16 ° C, respectively. Balanced fertilizer is applied through the water application system. The plants are grown for 10 to 23 days so that at the time of treatment the plants vary in a stage of 2 to 8 leaves. One treatment consists of compound 9, metsulfuron-methyl and chlorsulfuron-metsulfuron-methyl (5: 1) alone or in combination. The treatments are formulated in a non-phytotoxic solvent mixture which includes a surfactant and is applied as a spray to the foliar using a volume of 280-458 1 / ha. Each treatment is replicated three times. It is noted that the application solvent has no effect compared to untreated control plants. The treated plants and controls are maintained in the. greenhouse and water is applied as needed taking precaution not to wet the foliage during the first 24 hours after treatment. Effects on plants approximately 17 days after treatment are visually compared with untreated controls. The response ratings of the plants are calculated as the means of three duplicates, based on a scale of 0 to 100 where 0 is no effect and 1.00 is complete elimination. The Colby equation is used to determine the expected herbicidal effects from the mixtures. The expected additive effects and effects of the Colby equation are included in Table I. Table I - Observed and Expected Results of Compound 9 Alone and Combined with Metsulfuron-ethyl and with Clorsulfuron-Metsulfuron-Methyl (5: 1) * * Application rates are in grams of active ingredient per hectare (g a.i./ha). "Observed" is the observed effect. "Expected" is the expected effect calculated from the Colby equation. As can be seen from the results included in Table I, some of the observed results for weeds are greater than those expected from the Colby equation. Most notable is the greater effect than additive that is observed on alforjón, kochia and chenopodium. In addition, the results observed for almost all treatments on wheat are lower than those expected from the Colby equation, which suggests safety for the harvest.
TEST J This test evaluates the effect of mixtures of compound 58 with azimsulfuron on various plant species. Three plastic pots (approximately 16 cm in diameter) per dose are partially filled with black soil and sterilized Tama silt comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. The separate plantings for each of the three pots are as follows. Seeds of E.U.A. are planted of water duckweed (HETLI; Heteranthera limosa), African small flower sedge (CYPDI; Cyperus difformis) and purple amaryllis (AMMCO; Ammannia coccinea) in a 16 cm pot for each dose. The seeds of the plants of E.U.A. of sprangletop bearded (LEFUF; Leptochloa fusca ssp. fascicularis), a set of 9 or 10 rice seedlings seeded in water (ORYSW; Oryza sativa cv. "Japónica - M202") and a set of 6 transplanted rice seedlings (ORYSW; Oryza sativa cv. "Japónica - M2002") in a 16 cm pot for each dose. Seeds of E.U.A. weed (ECHCG; Echínochloa crus-galli), late aquatic weed (EC0R2; Echinochloa oryzicola), early aquatic weed (ECHOR; Echlnochloa oryzoides (and rice, from the forest (ECHCO; Echinochloa colona) in 16 cm pots; Each dose The plantations are sequential so that the crop and weed species are in a stage of 2.0 to 2.5 leaves at the time of the treatment The plants seeded in pots are grown in a greenhouse with day-night temperature adjustment of 29.5 / 26.7 ° C and supplemented balanced lighting is provided to maintain a photoperiod of 16 hours.The test pots are kept in the greenhouse until the end of the test.At the time of treatment, the test pots are flooded at 3 cm above the surface of the soil and then treated by application directly to the flooded water of the test compounds formulated in a non-phytotoxic solvent mixture which includes a surfactant. The pots are kept at a depth of 3 cm of water for the duration of the test. The treatments consist of compound 58 and azimsulfuron alone and combined. The effects of treatments on rice and weeds are evaluated visually by cooperation with untreated controls after 21 days. The response ratings of the plants are calculated as the means of three replicates and are summarized in table J. Classifications are based on a scale of 0 to 100, where 0 is no effect and 100 is complete elimination. A hyphen (-) response means that it is not a test result. The Colby equation is used to determine the expected herbicidal effects of the mixtures. The results and additive effects expected from the Colby equation are included in Table J. Table J - Observed and Expected Results of Compound 58 Alone and in Combination with Azimsulfon * * Application rates are grams of active ingredient per hectare (g a.i./ha). "Observed" is the observed effect. "Expected" is the expected effect calculated from the Colby equation.
TEST K Seeds of the plant species selected from the susceptible forms of sulfonylurea herbicide (SU-susceptible) and resistant to sulfonylurea herbicide (SU-resistant) of gallium (GALAP; Galium aparine) and wheat (TRZAW; Triticum aestivum) with post-germination applications of the test chemicals formulated in a non-phytotoxic solvent mixture which includes a surfactant. Plants are treated in the 2-3 leaf stage and in the 2 whorls stage for wheat and gallium, respectively. The treated plants and controls are maintained in a controlled growth environment for 15 days after which time all species are compared to the controls and evaluated visually. The classifications of plant responses, which are summarized in Table K, are based on a scale of 0 to 100, where 0 is no effect and 100 is complete elimination. A response with a hyphen (-) means that it is not a test result.
Table K - Results of Treatment of Wheat and Gallium Susceptible or Resistant to Sulphonylurea with Compounds 1 and 9 and Clorsulfuron As can be seen from table K, although chlorsulfuron has little effect on the sulfonylurea resistant biotype of Galium aparine in this test, the compounds 1 and 9 provide a good elimination of both resistant and susceptible biotypes.
TEST L This field study includes treatments consisting of compound 1 and nicosulfuron alone and combined in gilthead (Cirsium arvense) and daisy cones (Erigeron spp.). The plants vary from 20 to 30 cm in height at the time of application in the month of May in the vicinity of Newark, Delaware. Compound 1 is formulated as a wettable powder containing 25% active ingredient by weight. • Nicosulfuron is in the form of an Accent ™ herbicide, a formulation of water-dispersible granules containing 75% active ingredient by weight. The formulations are dispersed in water in the spray tank before treatment. The treatments are performed using a calibrated backpack type sprinkler to supply 224 1 per hectare (24 gallons per acre) to a 3 m x 9 m (10 ft x 30 ft) lot. Each treatment is doubled twice. The effects of the plants, approximately 55 days after the treatment, are compared visually with the untreated controls. The response ratings of the plants are calculated as the mean of the two duplicates, based on a scale of 0 to 100 where 0 is without effect and 100 is complete elimination. The Colby equation is used to determine the expected herbicidal effects of the mixture. The results and the expected additive effects of the Colby equation are included in table L.
Table L - Observed and Expected Results of Compound 1 Alone and Combined with Nicosulfuron * * Application rates are grams of active ingredient per hectare (g a.i./ha). "Observed" is the observed effect. "Expected" is the expected effect calculated from the Colby equation. Table L shows that a synergistic effect is ebidente in this test from the combination of compound 1 and nicosulfuron. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (43)

  1. CLAIMS Having described the invention as above, the content of the following claims is claimed as property: 1. A compound characterized in that it is selected from formula I, an N-oxide or an agriculturally suitable salt thereof, wherein: R1 is cyclopropyl optionally substituted with 1-5 of R5, isopropyl optionally substituted with 1-5 of R6 or phenyl optionally substituted with 1-3 of R7; R2 is ((O) jC (R15) (Rls)) kR; R is C02H or a herbicidally effective derivative of C02H; R3 is halogen, cyano, nitro, OR20, SR21 or N (R22) R23; R4 is -N (R24) R25 or -N02; each Rs and R6 is independently halogen, alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkoxy of 1 to 3 atoms from "carbon, haloalkoxy of 1 to 2 carbon atoms, alkylthio 1 to 3 carbon atoms or haloalkylthio of 1 to 2 carbon atoms; - each R7 is independently halogen, cyano, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halocycloalkyl of 3 to 6 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, haloalkoxyalkyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms carbon, haloalkynyl of 3 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkenyloxy of 2 to 4 carbon atoms, haloalkenyloxy of 2 to 4 carbon atoms, alkynyloxy from 3 to 4 carbon atoms, haloalkynyloxy of 3 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, haloalkylsulfinyl of 1 to 4 atoms of carbon, alkylsulfonyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 carbon atoms, alkenylthio of 2 to 4 carbon atoms, haloalkenylthio of 2 to 4 carbon atoms, alkenylsulfinyl of 2 to 4 carbon atoms, halokenylsulfinyl of 2 atoms. of carbon, alkenylsulfonyl of 2 to 4 carbon atoms, haloalkenylsulfonyl of 2 to 4 carbon atoms, alkynylthio of 3 to 4 carbon atoms, haloalkynylthio of 3 to 4 carbon atoms, alkynylsulfinyl of 3 to 4 carbon atoms, haloalkylsulfinyl of 3 to 4 carbon atoms, alkynylsulfonyl of 3 to 4 carbon atoms, haloalkynylsulfonyl of 3 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, dialkylamino of 2 to 8 carbon atoms, cycloalkylamino of 3 to 6 carbon atoms carbon, (alkyl of 4 to 6 carbon atoms) cycloalkylamino, alkylcarbonyl of 2 to 6 carbon atoms, alkoxycarbonyl of 2 to 6 carbon atoms, alkylaminocarbonyl of 2 to 6 carbon atoms, dialkylaminocarbonyl of 3 to 8 carbon atoms, trialkylsilyl of 3 to 6 carbon atoms, phenyl, phenoxy or 5- or 6-membered heteroaromatic rings, each phenyl ring, phenoxy and 5- or 6-membered heteroaromatic ring optionally substituted with one to three substitutes which are independently selected from R45; or two adjacent R7, taken together as -0CH20-, CH2CH20-, -0CH (CH3) 0-, -OC (CH3) 0-, -OCF20-, -CF2CF20-, OCF2CF20- or -CH = CH-CH = CH -; R 15 is H, halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms or alkylcarbonyloxy of 2 to 4 carbon atoms; - R16 is H, halogen, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms; or R15 and R16 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; R20 is H, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 3 carbon atoms; R21 is H, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 3 carbon atoms; R22 and R23 are independently H or alkyl of 1 to 4 carbon atoms; R24 is H, alkyl of 1 to 4 carbon atoms optionally substituted with 1-2 of R30, alkenyl of 2 to 4 carbon atoms optionally substituted with 1-2 of R31 or alkynyl of 2 to 4 carbon atoms optionally substituted with 1 -2 of R32; or R24 is C (= 0) R33, nitro, OR34, S (0) 2R35, N (R36) R37 or N = C (R62) RS3; R2S is H, alkyl of 1 to 4 carbon atoms optionally substituted with 1-2 of R30 or C (= 0) R33; or R24 and R25 are taken together as a radical selected from - (CH2) 4-, - (CH2) 5-, -CH2CH = CHCH2- and . (CH2) 20 (CH2) 2-, each radical is optionally substituted with 1-2 of R38; or R24 and R25 are taken together as = C (R39) N (R40) R41 or = C (R42) OR43; _ each R30, R31 and R32 is independently halogen, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 carbon atoms, haloalkylthio of 1 to 3 carbon atoms, amino, alkylamino of 1 to 3 carbon atoms, dialkylamino of 2 to 4 carbon atoms or alkoxycarbonyl of 2 to 4 carbon atoms; each R33 is independently H, alkyl of 1 to 14 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy or benzyloxy; R34 is H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms or CHR6eC (O) OR67; R 35 is alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 3 carbon atoms; R36 is H, alkyl of 1 to 4 carbon atoms or C (= 0) Re4; R37 is H or alkyl of 1 to 4 carbon atoms; each R38 is independently halogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 carbon atoms, haloalkylthio of 1 to 3 carbon atoms , amino, alkylamino of 1 to 3 carbon atoms, dialkylamino of 2 to 4 carbon atoms or alkoxycarbonyl of 2 to 4 carbon atoms; R39 is H or alkyl of 1 to 4 carbon atoms; R40 and R41 are independently H or alkyl of 1 to 4 carbon atoms; or R40 and R41 are taken together as - (CH2) 4-, - (CH) 5-, -CH2CH = CHCH2- or - (CH2) 20 (CH2) 2-; R42 is H or alkyl of 1 to 4 carbon atoms; R43 is alkyl of 1 to 4 carbon atoms; each R 45 is independently halogen, cyano, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, halocycloalkyl of 3 to 6 carbon atoms, alkenyl of 2 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, alkynyl of 3 to 4 carbon atoms, haloalkynyl of 3 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, alkylamino of 1 to 4 carbon atoms, dialkylamino of 2 to 8 carbon atoms, cycloalkylamino of 3 to 6 carbon atoms, (alkyl) cycloalkylamino of 4 to 6 carbon atoms, alkylcarbonyl of 2 to 4 carbon atoms, alkoxy carbonyl of 2 to 6 carbon atoms, alkylaminocarbonyl of 2 to 6 atoms of carbon, dialkylaminocarbonyl of 3 to 8 atoms carbon or trialkylsilyl having 3 to 6 carbon atoms; Re2 is H, alkyl of 1 to 4 carbon atoms or phenyl optionally substituted with 1-3 of RS5; R63 is H or alkyl of 1 to 4 carbon atoms; or R62 and R63 are taken together as - (CH2) 4- or - (CH2) 5-; R64 is H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy or benzyloxy; each R55 is independently CH3, Cl or OCH3; R66 is H, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; RS7 is H, alkyl of 1 to 4 carbon atoms or benzyl; j is 0 or 1; and k is 0 or 1; with the proviso that: (a) when K is 0, then j is 0; (b) when R2 is CH20Ra then Ra is optionally substituted H, alkyl or benzyl, then R3 is different from cyano; (c) when R1 is phenyl substituted by Cl in each of the meta positions, the phenyl is also substituted by R7 in the para position; (d) when R1 is phenyl substituted by R7 in the para position and R7 is different from terbutyl, cyano or optionally substituted phenyl; (e) when R1 is. cyclopropyl or isopropyl optionally with 1-5 of Rs, then R is different from C (= W) N '(Rb) S (0) 2 -Rc-Rd where W is 0, S, NRe or N0Re; Rb is hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms; Rc is a direct link or CHRf, 0, NRe or N0Re; Rd is an optionally substituted aromatic carbocyclic or heterocyclic radical having 5 to 6 ring atoms, the radical is optionally fused to a 5 or 6 membered aromatic or non-aromatic ring; each Re is independently H, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms or phenyl; Rf is H, alkyl of 1 to 3 carbon atoms or phenyl; and (f) the compound of formula I is different from diethyl 6-amino-5-nitro-2-phenyl-4-pyrimidinomalonate. 2. The compound according to claim 1, characterized in that: R2 is C02R12, CH2OR13, CH (OR46) (OR47), CHO, C (= N0RX4) H, C (= NNR48R49) H, (O) jC (R15 ) (R16) C02R17, C (= 0)? (R18) R19, C (= S) OR50, C (= 0) SRsl, C (= S) SR52 or C (=? RS3) YR54; R12 is H, -CH-. { C (0) 0 (CH2) m4-? = C (R55) 55; or a radical selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alkylcycloalkyl of 4 to 12 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl of 2 to 14 carbon atoms. carbon, alkynyl of 2 to 14 carbon atoms and phenyl, each radical is optionally substituted with 1-3 of R27; or R12 is a divalent radical that binds the carboxyl ester function C02R12 of each two pyrimidine ring systems of formula I, the divalent radical is selected from -CH2-, - (CH2) 2-, ~ (CH2) 3- and - CH (CH3) CH2-; R 13 is H, alkyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R28 or benzyl; R 14 is H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms or benzyl; R17 is alkyl of 1 to 10 carbon atoms optionally substituted with 1-3 of R29, or benzyl; R18 is H, alkyl of 1 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms or S (0) 2R57; R19 is H or alkyl of 1 to 4 carbon atoms; each R27 is independently halogen, cyano, hydroxycarbonyl, alkoxycarbonyl of 2 to 4 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 carbon atoms, dialkylamino of 2 to 4 carbon atoms, -CH-f-0 (CH2) _} - or phenyl optionally substituted with 1-3 of R44; or two of R27 are taken together as -OC (0) 0- or 0 (C (R58) (R58))!. ^ -; or two of R27 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R28 is independently halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 atoms of carbon or dialkylamino of 2 to 4 carbon atoms; or two of R28 are taken together as an oxygen atom to form, with the carbon atom to which they are attached, a carbonyl moiety; each R29 is independently halogen, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, haloalkylthio of 1 to 4 carbon atoms, amino, alkylamino of 1 to 4 atoms of carbon or dialkylamino of 2 to 4 carbon atoms; each R44 is independently halogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms, hydroxy, alkoxy of 1 to 4 carbon atoms, haloalkoxy of 1 to 3 carbon atoms, alkylthio of 1 to 3 atoms of carbon, haloalkylthio of 1 to 3 carbon atoms, amino, alkylamino of 1 to 3 carbon atoms, dialkylamino of 2 to 4 carbon atoms or nitro; R46 and R47 are independently alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 3 carbon atoms; or R46 and R47 are taken together as -CH2CH2-, -CH2CH (CH3> - or - (CH2) 3-; R48 is H, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkylcarbonyl from 2 to 4 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms or benzyl, R49 is H, alkyl of 1 to 4 carbon atoms or haloalkyl of 1 to 4 carbon atoms, R? 0, R51 and R52 are H or a radical selected from alkyl of 1 to 14 carbon atoms, cycloalkyl of 3 to 12 carbon atoms, alkylcycloalkyl of 4 to 12 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl of 2 to 14 atoms carbon and alkynyl of 2 to 14 carbon atoms, each radical is optionally substituted with 1-3 of R27; And it is O, S or NR61; R53 is H, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms, alkoxyalkyl of 2 to 4 carbon atoms, OH or alkoxy of 1 to 3 carbon atoms; R54 is alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms or alkoxyalkyl of 2 to 4 carbon atoms; or R53 and R54 are taken together as - (CH2) 2-, -CH2CH (CH3) - or - (CH2) 3-; R55 and R5e are independently alkyl of 1 to 4 carbon atoms; R57 is alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 3 carbon atoms or NRS9R60; each R58 is independently selected from H and alkyl of 1 to 4 carbon atoms; R59 and Rso are independently H or alkyl of 1 to 4 carbon atoms; R61 is H, alkyl of 1 to 3 carbon atoms, haloalkyl of 1 to 3 carbon atoms or alkoxyalkyl of 2 to 4 carbon atoms; m is an integer from 2 to 3; and n is an integer from 1 to 4. The compound according to claim 2, characterized in that R3 is halogen. The compound according to claim 2, characterized in that R1 is cyclopropyl or phenyl substituted with a halogen, methyl or methoxy radical in the para position and optionally with 1-2 radicals which are selected from halogen and methyl in other positions, and R4 is -N (R24) R25. 5. The compound according to claim 4, characterized in that R2 C02R12, CH2OR13, CHO or CH2C02R17. 6. The compound according to claim 5, characterized in that R24 is H, C (0) R33 or alkyl of 1 to 4 carbon atoms optionally substituted with R30; R2S is H or alkyl of 1 to 2 carbon atoms; or R24 and R25 are taken together as = C (R39) N (R40) R41. 7. The compound according to claim 6, characterized in that R2 is -C02R12; and R24 and R25 are H. The compound according to claim 7, characterized in that R12 is H, alkyl of 1 to 4 carbon atoms or benzyl. 9. The compound according to claim 1, characterized in that it is selected from the group consisting of: methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate 6-amino-5-bromo-2-cyclopropyl Ethyl 4-pyrimidine carboxylate, phenylmethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidine carboxylate, 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt, methyl-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylate, phenylmethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylate, 6-amino-5-chloro monosodium salt -2- cyclopropyl-4-pyrimidinecarboxylic acid, 6-amino-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylate, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylate of methyl, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylic acid ethyl ester, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylic acid, 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidine-carboxylic acid ethyl ester, 6-amino-2- (4-bromophenyl) -5-clo methyl ro-4-pyrimidine carboxylate, and 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidinecarboxylic acid. 10. A herbicidal mixture characterized in that it comprises a herbicidally effective amount of a compound according to claim 1 and an effective amount of at least one additional active ingredient that is selected from the group consisting of another herbicide and a herbicide sanitizer. 11. A herbicidal mixture, characterized in that it comprises synergistically effective amounts of a compound according to claim 1 and an auxin transport inhibitor. 12. A herbicidal composition, characterized in that it comprises a herbicidally effective amount of a compound according to claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent. 13. A method for eliminating unwanted vegetation growth, characterized in that it comprises contacting the vegetation in its environment with a herbicidally effective amount of a compound according to claim 1. 14. A herbicidal composition, characterized in that it comprises an amount herbicidally effective of a compound according to claim 1, an effective amount of at least one additional active ingredient that is selected from the group consisting of another herbicide and a herbicide sanitizer, and at least one of a surfactant, a diluent solid or a liquid diluent. 15. A compound, characterized in that it is 2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid. 16. A compound, characterized in that it is the acid 5-Chloro-2-cyclopropyl-1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acid. 17. A compound, characterized because it is acid 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid. 18. The compound according to claim 1, characterized in that it is selected from the group consisting of: methyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidine-carboxylate, 6-amino-5-bromo-2 ethyl-cyclopropyl-4-pyrimidine-carboxylate, phenylmethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidine-carboxylate, 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt , 6-amino-5-chloro-2-cyclopropyl-4'-pyrimidinecarboxylic acid, 6-amino-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylic acid methyl, 6-amino-5-chloro-2-cyclopropyl Phenylmethyl 4-pyrimidine carboxylate, 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monosodium salt, 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid, 6- ethyl-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylate, methyl 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylate, 6-amino-5-chloro- 2- (4-chlorophenyl) -4-pyrimidinecarboxylic acid ethyl ester, 6-amino-5-chloro-2- (4-chlorophen l) -4-pyrimidine-carboxylic acid, 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidine-carboxylic acid ethyl ester, 6-amino-2- (4-bromo-phenyl) -5-chloro-4 methyl-pyrimidine-carboxylate, and 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidinecarboxylic acid. 19. The compound of claim 18, characterized in that it is selected from the group consisting of: ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidine-carboxylate, 6-amino-5-chloro-2-cyclopropyl- Methyl 4-pyrimidine-carboxylate, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylic acid methyl, 6-amino-5-chloro-2- (4-chlorophenyl) -4- ethyl pyrimidine-carboxylate, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylic acid, 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidine-carboxylate ethyl, 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidine-carboxylic acid, 6-amino-2- (-bromofyl) -5-chloro-4-pyrimidine-carboxylic acid methyl ester, and 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid. 20. A compound according to claim 1, characterized in that it is 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylic acid. 21. A compound according to claim 1, characterized in that it is methyl 6-amino-5-bromop2-cyclopropyl-4-pyrimidinecarboxylate. 22. A compound according to claim 1, characterized in that it is methyl 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidinecarboxylate. 23. A compound according to claim 1, characterized in that it is ethyl 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidinecarboxylate. 24. A compound according to claim 1, characterized in that it is 6-amino-5-chloro-2- (4-chlorophenyl) -pyrimidinecarboxylic acid. 25. A compound according to claim 1, characterized in that it is 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid. 26. A compound according to claim 1, characterized in that it is ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate. 27. A compound according to claim 1, characterized in that it is methyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate. 28. A compound according to claim 1, characterized in that it is ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate. 29. A herbicidal mixture characterized in that it comprises a herbicidally effective amount of a compound of claims 18 or 19 and an effective amount of at least one additional active ingredient that is selected from the group consisting of another herbicide-herbicide sanitizer. The herbicidal mixture of claim 10, characterized in that the additional active ingredient is selected from the group consisting of: amidosulforon, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, etametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupirsulfuron, -methyl, flupirsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazametabenz-methyl, imazamox, imazapic, imazapir , imazaquin, imazaquin-ammonium, imazetapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, piribenzoxim, piriftalide , piriminobac-methyl, piritiobac, piritiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, tifensulfuron-meti lo, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron. The herbicidal mixture of claim 30, characterized in that the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients that are selected from the group consisting of: chlorsulfuron and flucarbazone-sodium; chlorsulfuron and sulfometuron-methyl; flumetsulam, nicosulfuron and rimsulfuron; mesosulfuron-methyl and yodosulfuron-methyl; metsulfuron-methyl and chlorsulfuron; metsulfuron-methyl and sulfometuron-methyl, • metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl; imazapyr and metsulfuron-methyl; imazapyr, metsulfuron-methyl and sulfometuron-methyl; imazapyr and sulfometuron-methyl; rimsulfuron and nicosulfuron; rimsulfuron and tifensulfuron-methyl; tifensulfuron-methyl and metsulfuron-methyl; tribenuron-methyl and metsulfuron-methyl; tribenuron-methyl and tifensulfuron-methyl; bensulfuron-methyl and metsulfuron-methyl; and metsulfuron-methyl and chlorimuron-ethyl. 32. The herbicidal mixture of claim 29, characterized in that the additional active ingredient is selected from the group consisting of: amidosulforon, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, etametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupirsulfuron, -methyl, flupirsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazametabenz-methyl, imazamox, imazapic, imazapir , imazaquin, imazaquin-ammonium, imazetapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, piribenzoxim, piriftalide , piriminobac-methyl, piritiobac, piritiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, tifensulfuron-methyl or, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron. 33. The herbicidal mixture of claim 32, characterized in that the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients that are selected from the group consisting of: chlorsulfuron and flucarbazone-sodium; chlorsulfuron and sulfometuron-methyl; flumetsulam, nicosulfuron and rimsulfuron; mesosulfuron-methyl and yodosulfuron-methyl; metsulfuron-methyl and chlorsulfuron; metsulfuron-methyl and sulfometuron-methyl; metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl; imazapyr and metsulfuron-methyl; imazapyr, metsulfuron-methyl and sulfometuron-methyl; imazapyr and sulfometuron-methyl; rimsulfuron and nicosulfuron; rimsulfuron and tifensulfuron-methyl; tifensulfuron-methyl and metsulfuron-methyl; tribenuron-methyl and metsulfuron-methyl; tribenuron-methyl and tifensulfuron-methyl; bensulfuron-methyl and metsulfuron-methyl; and metsulfuron-methyl and chlorimuron-ethyl. 34. A herbicidal mixture characterized in that it comprises synergistically effective amounts of a compound according to claims 18 or 19 and an auxin transport inhibitor. 35. The herbicidal mixture of claim 11, characterized in that the compound is selected from the group consisting of: ethyl 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylate, 6-amino-5-chloro-2 - Methyl cyclopropyl-4-pyrimidinecarboxylate, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylic acid methyl, 6-amino-5-chloro-2- (4-chlorophenyl) -4- ethyl pyrimidine-carboxylate, 6-amino-5-chloro-2- (4-chlorophenyl) -4-pyrimidine-carboxylic acid, 6-amino-2- (4-bromophenyl) -5-chloro-4-pyrimidine-carboxylate of ethyl, 6-amino-2- (4-bromo-phenyl) -5-chloro-4-pyrimidine-carboxylic acid, methyl 6-amino-2- (4-bromo-phenyl) -5-chloro-4-pyrimidinecarboxylate, and acid 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid, and the auxin transport inhibitor is diflufenzopyr. 36. The herbicidal mixture of claim 11, characterized in that the compound is ethyl 6-amino-5-bromo-2-cyclopropyl-4-pyrimidinecarboxylate and the auxin transport inhibitor is diflufenzopyr. 37. The herbicidal mixture of claim 29, characterized in that it further comprises at least one of a surfactant, a solid diluent or a liquid diluent. 38. The herbicidal mixture of claim 34, characterized in that it further comprises at least one of a surfactant, a solid diluent or a liquid diluent. 39. The herbicidal mixture of claim 37, characterized in that the additional active ingredient is selected from the group consisting of: amidosulforon, azimsulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, etametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupirsulfuron, -methyl, flupirsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazametabenz-methyl, imazamox, imazapic, imazapir , imazaquin, imazaquin-ammonium, imazetapyr, imazosulfuron, iodosulfuron-methyl, mesosulfuron-methyl, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, piribenzoxim, piriftalide , piriminobac-methyl, piritiobac, piritiobac-sodium, rimsulfuron, • sulfometuron-methyl, sulfosulfuron; tifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl and tritosulfuron. 40. The herbicidal mixture of claim 39, characterized in that the additional active ingredient is in combination with at least one other active ingredient to form a combination of active ingredients that are selected from the group consisting of: chlorsulfuron and flucarbazone-sodium; chlorsulfuron and sulfometuron-methyl; flumetsulam, nicosulfuron and rimsulfuron; mesosulfuron-methyl and yodosulfuron-methyl, - metsulfuron-methyl and chlorosulfuron; metsulfuron-methyl and sulfometuron-methyl; metsulfuron-methyl, thifensulfuron-methyl and tribenuron-methyl, -imazapyr and metsulfuron-methyl; imazapyr, metsulfuron-methyl and sulfometuron-methyl; imazapyr and sulfometuron-methyl; rimsulfuron and nicosulfuron; rimsulfuron and tifensulfuron-methyl; tifensulfuron-methyl and metsulfuron-methyl; tribenuron-methyl and metsulfuron-methyl; tribenuron-methyl and tifensulfuron-methyl; bensulfuron-methyl and metsulfuron-methyl; and metsulfuron-methyl and chlorimuron-ethyl. 41. The herbicidal mixture of claim 32, characterized in that the mixture has a greater effect than additive on weeds or a lesser effect than additive on crops or other desirable plants. 42. The herbicidal mixture of claim 33, characterized in that the mixture has a greater effect than additive on weeds or a lesser effect than additive on crops or other desirable plants. 43. A method for eliminating unwanted vegetation growth characterized in that it comprises contacting the vegetation to its environment with the herbicidal mixture of claim 32. 4. A method for eliminating unwanted vegetation growth characterized in that it comprises contacting the vegetation to its environment with the herbicidal mixture of claim 33. 45. A method for eliminating undesired vegetation growth, characterized in that it comprises contacting the vegetation or its environment with the herbicidal mixture of claim 3.
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